Substituted sulfonylureas

ABSTRACT

Substituted sulfonylureas of the formula I ##STR1## where the substituents and indices have the following meanings: X is oxygen or sulfur; 
     Z is nitrogen or methine (═CH--); 
     R 1  is halogen or substituted or unsubstituted C 1  -C 4  -alkoxycarbonyl or C 1  -C 3  -alkoxy, or a radical --CONR 6  R 7 , where 
     R 6  is hydrogen, C hd 1-C 8  -alkyl or C 1  -C 6  -alkoxy and 
     R 7  is hydrogen or C 1  -C 8  -alkyl; 
     R 2  is halogen or substituted or unsubstituted C 1  -C 4  -alkoxy or C 1  -C 4  -alkyl; 
     R 3  is C 1  -C 4  -alkyl, C hd 1-C 4  -alkylthio, C hd 1-C 4  -haloalkyl, C 1  -C 4  -haloalkoxy, C 1  -C 4  -haloalkylthio, halogen, cyano, nitro, amino, mono-C 1  -C 4  -alkylamino, di-C 1  -C 4  -alkylamino, C hd 2-C 6  -alkenyl, C 1  -C 4  -alkoxycarbonyl, C 1  -C 4  -alkanoyl or benzyl; a 5- or 6-membered saturated heterocycle which is attached by its nitrogen atom and which, besides methylene and a nitrogen, may also contain an oxygen or a sulfur atom; or, bonded to adjacent ring positions, --OCRR&#39;O--, where R and R&#39; are each hydrogen or C 1  -C 4  -alkyl; 
     R 4  is hydrogen or C 1  -C 4  -alkyl; 
     R 5  is halogen, C 1  -C 4  -alkyl, C 1  -C 4  -alkoxy, C 1  -C 4  -alkylthio or C 1  -C 4  -haloalkyl; 
     m is from 0 to 3 or, when R 3  is halogen, from 0 to 5, differences among the R 3  radicals being possible when m is 2 or 3; and 
     n is from 0 to 2, a difference between the R 5  radicals being possible when n is 2; 
     and environmentally acceptable salts thereof, processes for their manufacture, and their use as herbicidal agents.

This is a division of application Ser. No. 448,984, filed Dec. 12, 1989,now U.S. Pat. No. 5,032,167.

The present invention relates to substituted sulfonylureas of thegeneral formula I ##STR2## where the substituents and indices have thefollowing meanings: X is oxygen or sulfur;

Z is nitrogen or methine (═CH--);

R¹ is halogen, C₁ -C₄ -alkoxycarbonyl which may carry from one to threeof the following radicals: halogen, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy,C₁ -C₄ -alkylthio and/or C₁ -C₄ -haloalkylthio; C₁ -C₃ -alkoxy which maycarry from one to three of the following radicals: halogen, C₁ -C₄-alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio and/or C₁ -C₄-haloalkylthio; or a radical --CONR⁶ R⁷, where R⁶ is hydrogen, C₁ -C₈-alkyl or C₁ -C₆ -alkoxy and R⁷ is hydrogen or C₁ -C₈ -alkyl;

R² is halogen; C₁ -C₄ -alkoxy or C₁ -C₄ -alkyl which may each carry fromone to three of the following radicals: halogen, C₁ -C₄ -alkoxy and/orC₁ -C₄ -alkylthio;

R³ is C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄-haloalkyl, C₁ -C₄ -haloalkoxy, C₁ -C₄ -haloalkylthio, halogen, cyano,nitro, amino, mono-C₁ -C₄ -alkylamino, di-C₁ -C₄ -alkylamino, C₂ -C₆-alkenyl, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkanoyl or benzyl; a 5- or6-membered saturated heterocycle which is attached by its nitrogen atomand which, besides methylene and a nitrogen, may also contain an oxygenor sulfur atom; or, bonded to adjacent ring positions, --OCRR'O--, whereR and R' are each hydrogen or C₁ -C₄ -alkyl;

R⁴ is hydrogen or C₁ -C₄ -alkyl;

R⁵ is halogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio or C₁-C₄ -haloalkyl;

m is from 0 to 3 or, when R³ is halogen, from 0 to 5, differences amongthe R³ radicals being possible when m is 2 or 3; and

n is from 0 to 2, a difference between the R⁵ radicals being possiblewhen n is 2;

and to environmentally acceptable salts thereof.

The present invention further relates to processes for preparingcompounds I and to the use thereof as herbicides.

JP-A-58/126,872 discloses pyrimidyl- and triazinyl-sulfonylureas of theformula I' ##STR3## where the radicals have inter alia the followingmeanings: R is substituted or unsubstituted phenyl or phenoxy,

Y is nitrogen or methine,

A¹ and A² are each independently of the other hydrogen, halogen, alkyl,alkoxy, haloalkyl, alkylthioalkyl, phenylthio and/or phenoxy.

However, these compounds leave a lot to be desired as herbicides onaccount of the low selectivity with respect to harmful plants and onaccount of the relatively high application rates required.

It is an object of the present invention to provide novel compounds ofthe class of the substituted sulfonylureas with improved herbicidalproperties.

We have found that this object is achieved by the substitutedsulfonylureas I defined at the beginning.

In the reaction scheme below, which indicates methods for preparing I,the radicals ##STR4## have been replaced for greater clarity by φ1 andφ2 respectively. ##STR5##

The specific conditions for each of these methods are as follows:

A: A sulfonyl isocyanate II is reacted in a conventional manner(EP-A-7687) in an inert organic solvent in the absence or presence of abase with an approximately stoichiometric amount of a 2-aminohetarylether III at from 0° to 120° C., preferably at from 10° to 100° C.

This reaction is preferably carried out in acetonitrile, toluene ormethylene chloride in the presence of from 0 to 100 mole equivalents,preferably from 10 to 50 mole equivalents, of a tertiary amine such as1,4-diazabicyclo[2.2.2]octane (DABCO).

B: A corresponding sulfonyl carbamate of the formula IV is reacted in aconventional manner (EP-A-120,814) in an inert organic solvent at from0° to 120° C., preferably at from 10° to 100° C., with a 2-aminohetarylether III. A base, such as a tertiary amine base, may be added here tospeed up the reaction and improve the quality of the product.

This variation is preferably carried out in an aprotic polar solventsuch as dioxane or tetrahydrofuran in the presence of a tertiary aminesuch as p-dimethylaminopyridine and 1,4-diazabicyclo[2.2.2]octane.

C: A sulfonamide of the formula V is reacted in a conventional manner(EP-A-120,814) in an inert organic solvent with an approximatelystoichiometric amount of phenyl carbamate VI at from 0° to 120° C.,preferably at from 25° to 100° C. Again it is possible to add a basesuch as a tertiary amine. Particularly suitable tertiary amines for thispurpose are pyridine, the picolines, 2,4-and 2,6-lutidine,2,4,6-collidine, p-dimethylaminopyridine, 1,4-diazabicyclo[2.2.2]octane(DABCO) and 1,8-diazabicyclo[5.4.0]undec-7-ene, preferably1,4-diazabicyclo[2.2.2]octane and 1,8-diazabicyclo[5.4.0]undec-7-ene.

Again it is advantageous to use a solvent such as dioxane ortetrahydrofuran.

Preferably, the reaction is carried out under atmospheric pressure orunder a slightly superatmospheric pressure, for example at up to 5 bar,either batchwise or continuously.

The salts of the sulfonylureas are obtained by reaction with astoichiometric amount of a metal alcoholate in the absence or presenceof an inert organic solvent.

The sulfonamides of the formula V required as starting materials can beprepared from haloanthranilic esters by a Meerwein reaction (F. Muth inMethoden der Organischen Chemie (Houben-Weyl) volume 9, 557 (1955)) andsubsequent reaction of the resulting sulfonyl chloride with ammonia.

The aryloxy- or thioaryl-substituted pyrimidine or triazineintermediates required can be prepared by literature methods, asdescribed for example in J. Med. Chem. 29 (1986), 676, in J. Amer. Chem.Soc. 73 (1951), 2990, in Arch. Pharm. 296 (1963), 151, in Chem. Ber. 96(1963), 2909, in Bull. Chem. Soc. Jpn. 45 (1972), 3133, in Agric. Biol.Chem. 30 (1966), 896, and in Rec. Trav. Chim. Pays-Bas 64 (1945), 115,or similarly to the Examples given in the text below.

As regards biological activity, preference is given to the compounds ofthe formula I where substituents have the following meanings:

X is oxygen or sulfur;

Z is nitrogen or methine (═CH--);

R¹ is halogen such as fluorine, chlorine or bromine, in particularchlorine, alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl,propyloxycarbonyl, isopropyloxycarbonyl or butoxycarbonyl, in particularmethoxycarbonyl or ethoxycarbonyl, alkoxy such as methoxy, ethoxy,propyloxy or 1-methylethoxy, in particular ethoxy or 1-methylethoxy,which may each carry halogen as mentioned above, alkoxy as mentionedabove and also haloalkoxy such as trifluoromethoxy, difluoromethoxy,fluoromethoxy, trichloromethoxy, dichloromethoxy, chloromethoxy,difluorochloromethoxy, 1-fluoroethoxy, 2-fluoroethoxy or2,2,2-trifluoroethoxy, but in particular trifluoromethoxy ordifluoromethoxy, alkylthio such as methylthio, ethylthio, propylthio or1-methylethylthio, in particular methylthio, ethylthio and/orhaloalkylthio such as trifluoromethylthio, fluoromethylthio,1-trifluoromethylthio, fluoromethylthio, 1-fluoroethylthio,2-fluoroethylthio, chloromethylthio or 2-chloromethylthio, but inparticular trifluoromethylthio, chloromethylthio or 2-chloromethylthio,preferably in the 1- or 2-position, or corresponding alkoxy, and furtherbutyloxy, 1-methylpropyloxy, 2-methylpropyloxy or 1,1-dimethylethoxy,preferably in the 2- or 3-position; carbamoyl such as carboxamide,N-methylcarbamoyl, N,N-dimethylcarbamoyl, N-ethylcarbamoyl,N,N-diethylcarbamoyl, N-ethyl-N-methylcarbamoyl, in particular N-methyl-and N,N-dimethyl-carbamoyl; or hydroxamic ester groups, such asN-methoxycarbamoyl, N-methoxy-N-methylcarbamoyl or N-ethoxycarbamoyl,preferably N-methoxy-N-methylcarbamoyl;

R² is halogen as mentioned under R¹, preferably chlorine; alkoxy asmentioned under R¹, preferably methoxy; alkyl such as methyl, ethyl,propyl, 1-methyl-ethyl, butyl, 1-methylpropyl, 2-methylpropyl or1,1-dimethylpropyl, but in particular methyl or ethyl, which may each bemonosubstituted, disubstituted or trisubstituted by halogen and/oralkoxy such as mentioned under R¹ and/or by alkylthio such asmethylthio, ethylthio, propylthio or 1-methylethylthio;

R³ is alkyl as mentioned under R², preferably methyl or ethyl; alkoxy asmentioned under R¹, preferably methoxy, ethoxy or 1-methylethoxy;alkylthio as mentioned under R², in particular methylthio or ethylthio;haloalkyl such as trifluoromethyl, difluoromethyl, fluoromethyl,trichloromethyl, dichloromethyl, chloromethyl, difluorochloromethyl,1-fluoroethyl, 2-fluoroethyl or 2,2,2-trifluoroethyl, in particulartrifluoromethyl or difluoromethyl; haloalkoxy as mentioned under R¹,preferably 2-chloroethoxy or 2-fluoroethoxy; haloalkylthio as mentionedunder R¹, preferably 2-chloroethylthio or 2-fluoroethylthio; halogen asmentioned under R¹, in particular fluorine or chlorine, cyano, nitro,amino and/or amino which is monosubstituted or disubstituted by theabovementioned alkyl, such as methylamino, dimethylamino, ethylamino,diethylamino, methylethylamino, propylamino, N-methyl-N-propylamino,N-ethyl-N-propylamino, N,N-dipropylamino or N,N-di(1-methylethyl)amino,in particular N,N-dimethylamino; alkenyl such as ethenyl, 1-propenyl,2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl,1-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-1-propenyl,2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl,1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl,1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl,1,1-dimethyl-2-propenyl, 1-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl,1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl,4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl,3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl,2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl,1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl,4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl,3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl,1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl,1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl,1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl,2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl or 1-ethyl-2-methyl-2-propenyl, inparticular ethenyl, 1-propenyl, 2-propenyl or 1-methylethenyl;alkoxycarbonyl as mentioned in general and in particular under R¹ ; C₁-C₄ -alkanoyl such as propionyl and particularly acetyl and pivaloyl, orbenzyl; a 5- or 6-membered saturated heterocycle which is attached byits nitrogen atom and which, besides methylene and nitrogen, may alsocontain an oxygen or sulfur atom, such as pyrrolidinyl, piperidinyl,morpholinyl or thiomorpholinyl; or, bonded to adjacent ring positions,--O--CRR'--O--, where R and R' are each hydrogen or alkyl as mentionedunder R³, preferably hydrogen, methyl or ethyl;

the number of R³ substituents is from 0 to 3, but preferably 0, 1 or 2,or from 0 to 5 when R³ is halogen, and the groups may differ from eachother when m is equal to or greater than 2;

R⁴ is hydrogen or alkyl as mentioned under R², preferably hydrogen ormethyl; and R⁵ is halogen, alkyl, alkoxy, alkylthio or haloalkyl asmentioned under R³.

The number of R⁵ substituents is from 0 to 2, and the groups may differfrom each other when n is 2.

Particularly active compounds of the formula I are given in Tables A, B,C and D below.

                  TABLE A                                                         ______________________________________                                         ##STR6##                                                                     R.sup.1    R.sup.4 R.sup.2  (R.sup.3).sub.m                                   ______________________________________                                        CO.sub.2 CH.sub.3                                                                        H       Cl       H                                                 CO.sub.2 CH.sub.3                                                                        H       Cl       3-CH.sub.3                                        CO.sub.2 CH.sub.3                                                                        H       Cl       3-OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                        H       Cl       3-CF.sub.3                                        CO.sub.2 CH.sub.3                                                                        H       Cl       2-F                                               CO.sub.2 CH.sub.3                                                                        H       Cl       2-Cl                                              CO.sub.2 CH.sub.3                                                                        H       Cl       3-Cl                                              CO.sub.2 CH.sub.3                                                                        H       Cl       3-NO.sub.2                                        CO.sub.2 CH.sub.3                                                                        H       Cl       4-NO.sub.2                                        CO.sub.2 CH.sub.3                                                                        H       Cl       2-CN                                              CO.sub.2 CH.sub.3                                                                        H       Cl       2,6-OCH.sub.3,OCH.sub.3                           CO.sub.2 CH.sub.3                                                                        H       Cl       2,4,6-Cl,Cl,Cl                                    CO.sub.2 CH.sub.3                                                                        H       Cl       2-Cl,4-CF.sub.3                                   CO.sub.2 CH.sub.3                                                                        H       Cl       3-N(CH.sub.3).sub.2                               CO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              Cl       H                                                 CO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              Cl       3-CH.sub.3                                        CO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              Cl       3-OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              Cl       3-CF.sub.3                                        CO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              Cl       2-F                                               CO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              Cl       2-Cl                                              CO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              Cl       3-Cl                                              CO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              Cl       3-NO.sub.2                                        CO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              Cl       4-NO.sub.2                                        CO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              Cl       2-CN                                              CO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              Cl       2,6-OCH.sub.3,OCH.sub.3                           CO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              Cl       2,4,6-Cl,Cl,Cl                                    CO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              Cl       2-Cl,4-CF.sub.3                                   CO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              Cl       3-N(CH.sub.3).sub.2                               CO.sub.2 CH.sub.3                                                                        H       CH.sub.3 H                                                 CO.sub.2 CH.sub.3                                                                        H       CH.sub.3 3-CH.sub.3                                        CO.sub.2 CH.sub.3                                                                        H       CH.sub.3 3-OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                        H       CH.sub.3 3-CF.sub.3                                        CO.sub.2 CH.sub.3                                                                        H       CH.sub.3 2-F                                               CO.sub.2 CH.sub.3                                                                        H       CH.sub.3 2-Cl                                              CO.sub.2 CH.sub.3                                                                        H       CH.sub.3 3-Cl                                              CO.sub.2 CH.sub.3                                                                        H       CH.sub.3 3-NO.sub.2                                        CO.sub.2 CH.sub.3                                                                        H       CH.sub.3 4-NO.sub.2                                        CO.sub.2 CH.sub.3                                                                        H       CH.sub.3 2-CN                                              CO.sub.2 CH.sub.3                                                                        H       CH.sub.3 2,6-OCH.sub.3,OCH.sub.3                           CO.sub.2 CH.sub.3                                                                        H       CH.sub.3 2,4,6-Cl,Cl,Cl                                    CO.sub.2 CH.sub.3                                                                        H       CH.sub.3 2-Cl,4-CF.sub.3                                   CO.sub.2 CH.sub.3                                                                        H       CH.sub.3 3-N(CH.sub.3).sub.2                               CO.sub.2 CH.sub.3                                                                        H       CF.sub.3 H                                                 CO.sub.2 CH.sub.3                                                                        H       CF.sub.3 3-CH.sub.3                                        CO.sub.2 CH.sub.3                                                                        H       CF.sub.3 3-OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                        H       CF.sub.3 3-CF.sub.3                                        CO.sub.2 CH.sub.3                                                                        H       CF.sub.3 2-F                                               CO.sub.2 CH.sub.3                                                                        H       CF.sub.3 2-Cl                                              CO.sub.2 CH.sub.3                                                                        H       CF.sub.3 3-Cl                                              CO.sub.2 CH.sub.3                                                                        H       CF.sub.3 3-NO.sub.2                                        CO.sub.2 CH.sub.3                                                                        H       CF.sub.3 4-NO.sub.2                                        CO.sub.2 CH.sub.3                                                                        H       CF.sub.3 2-CN                                              CO.sub.2 CH.sub.3                                                                        H       CF.sub.3 2,6-OCH.sub.3,OCH.sub.3                           CO.sub.2 CH.sub.3                                                                        H       CF.sub.3 2,4,6-Cl,Cl,Cl                                    CO.sub.2 CH.sub.3                                                                        H       CF.sub.3 2-Cl,4-CF.sub.3                                   CO.sub.2 CH.sub.3                                                                        H       CF.sub.3 3-N(CH.sub.3).sub.2                               CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              2-OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              4-OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              2-OCH.sub.2 CH.sub.3                              CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              3-OCH.sub.2 CH.sub.3                              CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              4-OCH.sub.2 CH.sub.3                              CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              2-OCH(CH.sub.3).sub.2                             CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              3-OCH(CH.sub.3).sub.2                             CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              4-OCH(CH.sub.3).sub.2                             CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              2-O(CH.sub.2).sub.2 CH.sub.3                      CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              3-O(CH.sub.2).sub.2 CH.sub.3                      CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              4-O(CH.sub.2).sub.2 CH.sub.3                      CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              2-OC(CH.sub.3).sub.3                              CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              3-OC(CH.sub.3).sub.3                              CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              4-OC(CH.sub.3).sub.3                              CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              2,3-OCH.sub.3,OCH.sub.3                           CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              2,4-OCH.sub.3,OCH.sub.3                           CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              2,5-OCH.sub.3,OCH.sub.3                           CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              3,4-OCH.sub.3,OCH.sub.3                           CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              3,5-OCH.sub.3,OCH.sub.3                           CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              2,3,4-OCH.sub.3,OCH.sub.3,OCH.sub.3               CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              2,3,5-OCH.sub.3,OCH.sub.3,OCH.sub. 3              CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              2,4,6-OCH.sub.3,OCH.sub.3,OCH.sub.3               CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              3,4,5-OCH.sub.3,OCH.sub.3,OCH.sub.3               CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              H                                                 CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              3-CH.sub.3                                        CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              3-OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              3-CF.sub.3                                        CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              2-F                                               CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              2-Cl                                              CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              3-Cl                                              CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              3-NO.sub.2                                        CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              4-NO.sub.2                                        CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              2-CN                                              CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              2,6-OCH.sub.3,OCH.sub.3                           CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              2,4,6-Cl,Cl,Cl                                    CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              2-Cl,4-CF.sub.3                                   CO.sub.2 CH.sub.3                                                                        H       OCH.sub.3                                                                              3-N(CH.sub.3).sub.2                               Cl         H       Cl       H                                                 Cl         H       Cl       3-CH.sub.3                                        Cl         H       Cl       3-OCH.sub.3                                       Cl         H       Cl       3-CF.sub.3                                        Cl         H       Cl       2-F                                               Cl         H       Cl       2-Cl                                              Cl         H       Cl       3-Cl                                              Cl         H       Cl       3-NO.sub.2                                        Cl         H       Cl       4-NO.sub.2                                        Cl         H       Cl       2-CN                                              Cl         H       Cl       2,6-OCH.sub. 3,OCH.sub.3                          Cl         H       Cl       2,4,6-Cl,Cl,Cl                                    Cl         H       Cl       2-Cl,4-CF.sub.3                                   Cl         H       Cl       3-N(CH.sub.3).sub.2                               Cl         CH.sub.3                                                                              Cl       H                                                 Cl         CH.sub.3                                                                              Cl       3-CH.sub.3                                        Cl         CH.sub.3                                                                              Cl       3-OCH.sub.3                                       Cl         CH.sub.3                                                                              Cl       3-CF.sub.3                                        Cl         CH.sub.3                                                                              Cl       2-F                                               Cl         CH.sub.3                                                                              Cl       2-Cl                                              Cl         CH.sub.3                                                                              Cl       3-Cl                                              Cl         CH.sub.3                                                                              Cl       3-NO.sub.2                                        Cl         CH.sub.3                                                                              Cl       4-NO.sub.2                                        Cl         CH.sub.3                                                                              Cl       2-CN                                              Cl         CH.sub.3                                                                              Cl       2,6-OCH.sub.3,OCH.sub.3                           Cl         CH.sub.3                                                                              Cl       2,4,6-Cl,Cl,Cl                                    Cl         CH.sub.3                                                                              Cl       2-Cl,4-CF.sub.3                                   Cl         CH.sub.3                                                                              Cl       3-N(CH.sub.3).sub.2                               Cl         H       CH.sub.3 H                                                 Cl         H       CH.sub.3 3-CH.sub.3                                        Cl         H       CH.sub.3 3-OCH.sub.3                                       Cl         H       CH.sub.3 3-CF.sub.3                                        Cl         H       CH.sub.3 2-F                                               Cl         H       CH.sub.3 2-Cl                                              Cl         H       CH.sub.3 3-Cl                                              Cl         H       CH.sub.3 3-NO.sub.2                                        Cl         H       CH.sub.3 4-NO.sub.2                                        Cl         H       CH.sub.3 2-CN                                              Cl         H       CH.sub.3 2,6-OCH.sub.3,OCH.sub.3                           Cl         H       CH.sub.3 2,4,6-Cl,Cl,Cl                                    Cl         H       CH.sub.3 2-Cl,4-CF.sub.3                                   Cl         H       CH.sub.3 3-N(CH.sub.3).sub.2                               Cl         H       CF.sub.3 H                                                 Cl         H       CF.sub.3 3-CH.sub.3                                        Cl         H       CF.sub.3 3-OCH.sub.3                                       Cl         H       CF.sub.3 3-CF.sub.3                                        Cl         H       CF.sub.3 2-F                                               Cl         H       CF.sub.3 2-Cl                                              Cl         H       CF.sub.3 3-Cl                                              Cl         H       CF.sub.3 3-NO.sub.2                                        Cl         H       CF.sub.3 4-NO.sub.2                                        Cl         H       CF.sub.3 2-CN                                              Cl         H       CF.sub.3 2,6-OCH.sub.3,OCH.sub.3                           Cl         H       CF.sub.3 2,4,6-Cl,Cl,Cl                                    Cl         H       CF.sub.3 2-Cl,4-CF.sub.3                                   Cl         H       CF.sub.3 3-N(CH.sub.3).sub.2                               Cl         H       OCH.sub.3                                                                              H                                                 Cl         H       OCH.sub.3                                                                              3-CH.sub.3                                        Cl         H       OCH.sub.3                                                                              3-OCH.sub.3                                       Cl         H       OCH.sub.3                                                                              3-CF.sub.3                                        Cl         H       OCH.sub.3                                                                              2-F                                               Cl         H       OCH.sub.3                                                                              2-Cl                                              Cl         H       OCH.sub.3                                                                              3-Cl                                              Cl         H       OCH.sub.3                                                                              3-NO.sub.2                                        Cl         H       OCH.sub.3                                                                              4-NO.sub.2                                        Cl         H       OCH.sub.3                                                                              2-CN                                              Cl         H       OCH.sub.3                                                                              2,6-OCH.sub.3,OCH.sub.3                           Cl         H       OCH.sub.3                                                                              2,4,6-Cl,Cl,Cl                                    Cl         H       OCH.sub.3                                                                              2-Cl,4-CF.sub.3                                   Cl         H       OCH.sub.3                                                                              3-N(CH.sub.3).sub.2                               Cl         H       OCH.sub.3                                                                              2-OCH.sub.3                                       Cl         H       OCH.sub.3                                                                              4-OCH.sub.3                                       Cl         H       OCH.sub.3                                                                              2-OCH.sub.2 CH.sub.3                              Cl         H       OCH.sub.3                                                                              3-OCH.sub.2 CH.sub.3                              Cl         H       OCH.sub.3                                                                              4-OCH.sub.2 CH.sub.3                              Cl         H       OCH.sub.3                                                                              2-OCH(CH.sub.3).sub.2                             Cl         H       OCH.sub.3                                                                              3-OCH(CH.sub.3).sub.2                             Cl         H       OCH.sub.3                                                                              4-OCH(CH.sub.3).sub.2                             Cl         H       OCH.sub.3                                                                              2-O(CH.sub.2).sub.2 CH.sub.3                      Cl         H       OCH.sub.3                                                                              3-O(CH.sub.2).sub.2 CH.sub.3                      Cl         H       OCH.sub.3                                                                              4-O(CH.sub.2).sub.2 CH.sub.3                      Cl         H       OCH.sub.3                                                                              2-OC(CH.sub.3).sub.3                              Cl         H       OCH.sub.3                                                                              3-OC(CH.sub.3).sub.3                              Cl         H       OCH.sub.3                                                                              4-OC(CH.sub.3).sub.3                              Cl         H       OCH.sub.3                                                                              2,3-OCH.sub.3,OCH.sub.3                           Cl         H       OCH.sub.3                                                                              2,4-OCH.sub.3,OCH.sub.3                           Cl         H       OCH.sub.3                                                                              2,5-OCH.sub.3,OCH.sub.3                           Cl         H       OCH.sub.3                                                                              3,4-OCH.sub.3,OCH.sub.3                           Cl         H       OCH.sub.3                                                                              3,5-OCH.sub.3,OCH.sub.3                           Cl         H       OCH.sub.3                                                                              2,3,4-OCH.sub.3,OCH.sub.3,OCH.sub.3               Cl         H       OCH.sub.3                                                                              2,3,5-OCH.sub.3,OCH.sub.3,OCH.sub.3               Cl         H       OCH.sub.3                                                                              2,4,6-OCH.sub.3,OCH.sub.3,OCH.sub.3               Cl         H       OCH.sub.3                                                                              3,4,5-OCH.sub.3,OCH.sub.3,OCH.sub.3               CO.sub.2 C.sub.2 H.sub.5                                                                 H       Cl       H                                                 CO.sub.2 C.sub.2 H.sub.5                                                                 H       CH.sub.3 3-SCH.sub.3                                       CO.sub.2 C.sub.2 H.sub.5                                                                 CH.sub.3                                                                              CH.sub.3 2-O(CH.sub.2).sub.2 Cl                            CO.sub.2 C.sub.2 H.sub.5                                                                 H       Cl       3-OCCl.sub.3                                      CO.sub.2 C.sub.2 H.sub.5                                                                 H       OCH.sub.3                                                                              4-OCH.sub.2 F                                     CO.sub.2 C.sub.2 H.sub.5                                                                 H       OCH.sub.3                                                                              4-OCHF.sub.2                                      CO.sub.2 C.sub.3 H.sub.7                                                                 H       CF.sub.3 3-O(CH.sub.2).sub.2 F                             CO.sub.2 C.sub.3 H.sub.7                                                                 H       CF.sub.3 2-S(CH.sub.2).sub.2 Cl                            CO.sub.2 C.sub.3 H.sub.7                                                                 H       CCl.sub.3                                                                              2-S(CH.sub.2).sub.2 F                             CO.sub.2 C.sub.3 H.sub.7                                                                 H       CH.sub.3 2-SCF.sub.3                                       CO.sub.2 C.sub.3 H.sub.7                                                                 CH.sub.3                                                                              Cl       4-SCHF.sub.2                                      CONH(CH.sub.3)                                                                           H       Cl       2-OCH.sub.3                                       CONH(CH.sub.3)                                                                           H       CH.sub.3 3-OCH.sub.3                                       CON(CH.sub.3).sub.2                                                                      H       Cl       2-OCH.sub.3                                       CON(CH.sub.3).sub.2                                                                      H       CH.sub.3 3-OCH.sub.3                                       CON(CH.sub.3).sub.2                                                                      H       OCH.sub.3                                                                              4-OCH.sub.3                                       CON(CH.sub.3).sub.2                                                                      H       CF.sub.3 2-OCH.sub.3                                       CON(CH.sub.3).sub.2                                                                      H       OC.sub.2 H.sub.5                                                                       2-SCH.sub.3                                       CON(CH.sub.3).sub.2                                                                      H       OC.sub.2 H.sub.5                                                                       3-OCF.sub.3                                       CON(CH.sub.3)OCH.sub.3                                                                   H       CH.sub.3 2-OCH.sub.3                                       CON(CH.sub.3)OCH.sub.3                                                                   H       OCH.sub.3                                                                              3-OCH.sub.3                                       CON(CH.sub.3)OCH.sub.3                                                                   H       Cl       2-OCH.sub.3                                       CO.sub.2 (CH.sub.2).sub.2 Cl                                                             H       Cl       2-N(CH.sub.3).sub.2                               CO.sub.2 (CH.sub.2).sub.2 OCH.sub.3                                                      H       Cl       2-CN                                              CO.sub.2 (CH.sub.2).sub. 2 OC.sub.2 H.sub.5                                              CH.sub.3                                                                              Cl       2-NO.sub.2                                        CO.sub.2 (CH.sub.2).sub.2 OCF.sub.3                                                      H       Cl       2,3-Cl,Cl                                         OCH.sub.3  H       Cl       2-Cl                                              OCH.sub.3  H       Cl       3-NO.sub.2                                        OC.sub.2 H.sub.5                                                                         H       Cl       4-CN                                              O(CH.sub.2).sub.2 Cl                                                                     H       CH.sub.3 3-CH.sub.3                                        O(CH.sub.2).sub.2 F                                                                      CH.sub.3                                                                              CH.sub.3 2-Cl,4-CF.sub.4                                   O(CH.sub.2).sub.2 OCH.sub.3                                                              CH.sub.3                                                                              CH.sub.3 2,3,5-Cl,Cl,Cl                                    O(CH.sub.2).sub.2 OCH.sub.3                                                              CH.sub.3                                                                              CH.sub.3 3-N(CH.sub.3).sub.2                               O(CH.sub.2).sub.2 SCH.sub.3                                                              CH.sub.3                                                                              CH.sub.3 4-OCH.sub.3                                       O(CH.sub.2).sub.2 SCH.sub.3                                                              CH.sub.3                                                                              OCH.sub.3                                                                              2,4-Cl,Cl                                         O(CH.sub.2).sub.2 SCF.sub.3                                                              CH.sub.3                                                                              OCH.sub.3                                                                              2-OCH.sub.3                                       ______________________________________                                    

                  TABLE B                                                         ______________________________________                                         ##STR7##                                                                     R.sup.1       R.sup.4 R.sup.2  (R.sup.3).sub.m                                ______________________________________                                        CO.sub.2 CH.sub.3                                                                           H       Cl       H                                              CO.sub.2 CH.sub.3                                                                           H       Cl       3-CH.sub.3                                     CO.sub.2 CH.sub.3                                                                           H       Cl       3-OCH.sub.3                                    CO.sub.2 CH.sub.3                                                                           H       Cl       3-CF.sub.3                                     CO.sub.2 CH.sub.3                                                                           H       Cl       2-F                                            CO.sub.2 CH.sub.3                                                                           H       Cl       2-Cl                                           CO.sub.2 CH.sub.3                                                                           H       Cl       3-Cl                                           CO.sub.2 CH.sub.3                                                                           H       Cl       3-NO.sub.2                                     CO.sub.2 CH.sub.3                                                                           H       Cl       4-NO.sub.2                                     CO.sub.2 CH.sub.3                                                                           H       Cl       2-CN                                           CO.sub.2 CH.sub.3                                                                           H       Cl       2,6-OCH.sub.3,OCH.sub.3                        CO.sub.2 CH.sub.3                                                                           H       Cl       2,4,6-Cl,Cl,Cl                                 CO.sub.2 CH.sub.3                                                                           H       Cl       2-Cl,4-CF.sub.3                                CO.sub.2 CH.sub.3                                                                           H       Cl       3-N(CH.sub.3).sub.2                            CO.sub.2 CH.sub.3                                                                           CH.sub.3                                                                              Cl       H                                              CO.sub.2 CH.sub.3                                                                           CH.sub.3                                                                              Cl       3-CH.sub.3                                     CO.sub.2 CH.sub.3                                                                           CH.sub.3                                                                              Cl       3-OCH.sub.3                                    CO.sub.2 CH.sub.3                                                                           CH.sub.3                                                                              Cl       3-CF.sub.3                                     CO.sub.2 CH.sub.3                                                                           CH.sub.3                                                                              Cl       2-F                                            CO.sub.2 CH.sub.3                                                                           CH.sub.3                                                                              Cl       2-Cl                                           CO.sub.2 CH.sub.3                                                                           CH.sub.3                                                                              Cl       3-Cl                                           CO.sub.2 CH.sub.3                                                                           CH.sub.3                                                                              Cl       3-NO.sub.2                                     CO.sub.2 CH.sub.3                                                                           CH.sub.3                                                                              Cl       4-NO.sub.2                                     CO.sub.2 CH.sub.3                                                                           CH.sub.3                                                                              Cl       2-CN                                           CO.sub.2 CH.sub.3                                                                           CH.sub.3                                                                              Cl       2,6-OCH.sub.3,OCH.sub.3                        CO.sub.2 CH.sub.3                                                                           CH.sub.3                                                                              Cl       2,4,6-Cl,Cl,Cl                                 CO.sub.2 CH.sub.3                                                                           CH.sub.3                                                                              Cl       2-Cl,4-CF.sub.3                                CO.sub.2 CH.sub.3                                                                           CH.sub.3                                                                              Cl       3-N(CH.sub.3).sub.2                            CO.sub.2 CH.sub.3                                                                           H       CH.sub.3 H                                              CO.sub.2 CH.sub.3                                                                           H       CH.sub.3 3-CH.sub.3                                     CO.sub.2 CH.sub.3                                                                           H       CH.sub.3 3-OCH.sub.3                                    CO.sub.2 CH.sub.3                                                                           H       CH.sub.3 3-CF.sub.3                                     CO.sub.2 CH.sub.3                                                                           H       CH.sub.3 2-F                                            CO.sub.2 CH.sub.3                                                                           H       CH.sub.3 2-Cl                                           CO.sub.2 CH.sub.3                                                                           H       CH.sub.3 3-Cl                                           CO.sub.2 CH.sub.3                                                                           H       CH.sub.3 3-NO.sub.2                                     CO.sub.2 CH.sub.3                                                                           H       CH.sub.3 4-NO.sub.2                                     CO.sub.2 CH.sub.3                                                                           H       CH.sub.3 2-CN                                           CO.sub.2 CH.sub.3                                                                           H       CH.sub.3 2,6-OCH.sub.3,OCH.sub.3                        CO.sub.2 CH.sub.3                                                                           H       CH.sub.3 2,4,6-Cl,Cl,Cl                                 CO.sub.2 CH.sub.3                                                                           H       CH.sub.3 2-Cl,4-CF.sub.3                                CO.sub.2 CH.sub.3                                                                           H       CH.sub.3 3-N(CH.sub.3).sub.2                            CO.sub.2 CH.sub.3                                                                           H       CF.sub.3 H                                              CO.sub.2 CH.sub.3                                                                           H       CF.sub.3 3-CH.sub.3                                     CO.sub.2 CH.sub.3                                                                           H       CF.sub.3 3-OCH.sub.3                                    CO.sub.2 CH.sub.3                                                                           H       CF.sub.3 3-CF.sub.3                                     CO.sub.2 CH.sub.3                                                                           H       CF.sub.3 2-F                                            CO.sub.2 CH.sub.3                                                                           H       CF.sub.3 2-Cl                                           CO.sub.2 CH.sub.3                                                                           H       CF.sub.3 3-Cl                                           CO.sub.2 CH.sub.3                                                                           H       CF.sub.3 3-NO.sub.2                                     CO.sub.2 CH.sub.3                                                                           H       CF.sub.3 4-NO.sub.2                                     CO.sub.2 CH.sub.3                                                                           H       CF.sub.3 2-CN                                           CO.sub.2 CH.sub.3                                                                           H       CF.sub.3 2,6-OCH.sub.3,OCH.sub.3                        CO.sub.2 CH.sub.3                                                                           H       CF.sub.3 2,4,6-Cl,Cl,Cl                                 CO.sub.2 CH.sub.3                                                                           H       CF.sub.3 2-Cl,4-CF.sub.3                                CO.sub.2 CH.sub.3                                                                           H       CF.sub.3 3-N(CH.sub.3).sub.2                            CO.sub.2 CH.sub.3                                                                           H       OCH.sub.3                                                                              H                                              CO.sub.2 CH.sub.3                                                                           H       OCH.sub.3                                                                              3-CH.sub.3                                     CO.sub.2 CH.sub.3                                                                           H       OCH.sub.3                                                                              3-OCH.sub.3                                    CO.sub.2 CH.sub.3                                                                           H       OCH.sub.3                                                                              3-CF.sub.3                                     CO.sub. 2 CH.sub.3                                                                          H       OCH.sub.3                                                                              2-F                                            CO.sub.2 CH.sub.3                                                                           H       OCH.sub.3                                                                              2-Cl                                           CO.sub.2 CH.sub.3                                                                           H       OCH.sub.3                                                                              3-Cl                                           CO.sub.2 CH.sub.3                                                                           H       OCH.sub.3                                                                              3-NO.sub.2                                     CO.sub.2 CH.sub.3                                                                           H       OCH.sub.3                                                                              4-NO.sub.2                                     CO.sub.2 CH.sub.3                                                                           H       OCH.sub.3                                                                              2-CN                                           CO.sub.2 CH.sub.3                                                                           H       OCH.sub.3                                                                              2,6-OCH.sub.3,OCH.sub.3                        CO.sub.2 CH.sub.3                                                                           H       OCH.sub.3                                                                              2,4,6-Cl,Cl,Cl                                 CO.sub.2 CH.sub.3                                                                           H       OCH.sub.3                                                                              2-Cl,4-CF.sub.3                                CO.sub.2 CH.sub.3                                                                           H       OCH.sub.3                                                                              3-N(CH.sub.3).sub.2                            Cl            H       Cl       H                                              Cl            H       Cl       3-CH.sub.3                                     Cl            H       Cl       3-OCH.sub.3                                    Cl            H       Cl       3-CF.sub.3                                     Cl            H       Cl       2-F                                            Cl            H       Cl       2-Cl                                           Cl            H       Cl       3-Cl                                           Cl            H       Cl       3-NO.sub.2                                     Cl            H       Cl       4-NO.sub.2                                     Cl            H       Cl       2-CN                                           Cl            H       Cl       2,6-OCH.sub.3,OCH.sub.3                        Cl            H       Cl       2,4,6-Cl,Cl,Cl                                 Cl            H       Cl       2-Cl,4-CF.sub.3                                Cl            H       Cl       3-N(CH.sub.3).sub.2                            Cl            CH.sub.3                                                                              Cl       H                                              Cl            CH.sub.3                                                                              Cl       3-CH.sub.3                                     Cl            CH.sub.3                                                                              Cl       3-OCH.sub.3                                    Cl            CH.sub.3                                                                              Cl       3-CF.sub.3                                     Cl            CH.sub.3                                                                              Cl       2-F                                            Cl            CH.sub.3                                                                              Cl       2-Cl                                           Cl            CH.sub.3                                                                              Cl       3-Cl                                           Cl            CH.sub.3                                                                              Cl       3-NO.sub.2                                     Cl            CH.sub.3                                                                              Cl       4-NO.sub.2                                     Cl            CH.sub.3                                                                              Cl       2-CN                                           Cl            CH.sub.3                                                                              Cl       2,6-OCH.sub.3,OCH.sub.3                        Cl            CH.sub.3                                                                              Cl       2,4,6-Cl,Cl,Cl                                 Cl            CH.sub.3                                                                              Cl       2-Cl,4-CF.sub.3                                Cl            CH.sub.3                                                                              Cl       3-N(CH.sub.3).sub.2                            Cl            H       CH.sub.3 H                                              Cl            H       CH.sub.3 3-CH.sub.3                                     Cl            H       CH.sub.3 3-OCH.sub.3                                    Cl            H       CH.sub.3 3-CF.sub.3                                     Cl            H       CH.sub.3 2-F                                            Cl            H       CH.sub.3 2-Cl                                           Cl            H       CH.sub.3 3-Cl                                           Cl            H       CH.sub.3 3-NO.sub.2                                     Cl            H       CH.sub.3 4-NO.sub.2                                     Cl            H       CH.sub.3 2-CN                                           Cl            H       CH.sub.3 2,6-OCH.sub.3,OCH.sub.3                        Cl            H       CH.sub.3 2,4,6-Cl,Cl,Cl                                 Cl            H       CH.sub.3 2-Cl,4-CF.sub.3                                Cl            H       CH.sub.3 3-N(CH.sub.3).sub.2                            Cl            H       CF.sub.3 H                                              Cl            H       CF.sub.3 3-CH.sub.3                                     Cl            H       CF.sub.3 3-OCH.sub.3                                    Cl            H       CF.sub.3 3-CF.sub.3                                     Cl            H       CF.sub.3 2-F                                            Cl            H       CF.sub.3 2-Cl                                           Cl            H       CF.sub.3 3-Cl                                           Cl            H       CF.sub.3 3-NO.sub.2                                     Cl            H       CF.sub.3 4-NO.sub.2                                     Cl            H       CF.sub.3 2-CN                                           Cl            H       CF.sub.3 2,6-OCH.sub.3,OCH.sub.3                        Cl            H       CF.sub.3 2,4,6-Cl,Cl,Cl                                 Cl            H       CF.sub.3 2-Cl,4-CF.sub.3                                Cl            H       CF.sub.3 3-N(CH.sub.3 ).sub.2                           Cl            H       OCH.sub.3                                                                              H                                              Cl            H       OCH.sub.3                                                                              3-CH.sub.3                                     Cl            H       OCH.sub.3                                                                              3-OCH.sub.3                                    Cl            H       OCH.sub.3                                                                              3-CF.sub.3                                     Cl            H       OCH.sub.3                                                                              2-F                                            Cl            H       OCH.sub.3                                                                              2-Cl                                           Cl            H       OCH.sub.3                                                                              3-Cl                                           Cl            H       OCH.sub.3                                                                              3-NO.sub.2                                     Cl            H       OCH.sub.3                                                                              4-NO.sub.2                                     Cl            H       OCH.sub.3                                                                              2-CN                                           Cl            H       OCH.sub.3                                                                              2,6-OCH.sub.3,OCH.sub.3                        Cl            H       OCH.sub.3                                                                              2,4,6-Cl,Cl,Cl                                 Cl            H       OCH.sub.3                                                                              2-Cl,4-CF.sub.3                                Cl            H       OCH.sub.3                                                                              3-N(CH.sub.3).sub.2                            CO.sub.2 C.sub.2 H.sub.5                                                                    H       Cl       H                                              CO.sub.2 C.sub.2 H.sub.5                                                                    H       CH.sub.3 3-SCH.sub.3                                    CO.sub.2 C.sub.2 H.sub.5                                                                    CH.sub.3                                                                              CH.sub.3 2-O(CH.sub.2).sub.2 Cl                         CO.sub.2 C.sub.2 H.sub.5                                                                    H       Cl       3-OCCl.sub.3                                   CO.sub.2 C.sub.2 H.sub.5                                                                    H       OCH.sub.3                                                                              4-OCH.sub.2 F                                  CO.sub.2 C.sub.2 H.sub.5                                                                    H       OCH.sub.3                                                                              4-OCHF.sub.2                                   CO.sub.2 C.sub.3 H.sub.7                                                                    H       CF.sub.3 3-O(CH.sub.2).sub.2 F                          CO.sub.2 C.sub.3 H.sub.7                                                                    H       CF.sub.3 2-S(CH.sub.2).sub.2 Cl                         CO.sub.2 C.sub.3 H.sub.7                                                                    H       CCl.sub.3                                                                              2-S(CH.sub.2).sub.2 F                          CO.sub.2 C.sub.3 H.sub.7                                                                    H       CH.sub.3 2-SCF.sub.3                                    CO.sub.2 C.sub.3 H.sub.7                                                                    CH.sub.3                                                                              Cl       4-SCHF.sub.2                                   CONH(CH.sub.3)                                                                              H       Cl       2-OCH.sub.3                                    CONH(CH.sub.3)                                                                              H       CH.sub.3 3-OCH.sub.3                                    CON(CH.sub.3).sub.2                                                                         H       Cl       2-OCH.sub.3                                    CON(CH.sub.3).sub.2                                                                         H       CH.sub.3 3-OCH.sub.3                                    CON(CH.sub.3).sub.2                                                                         H       OCH.sub.3                                                                              4-OCH.sub.3                                    CON(CH.sub.3).sub.2                                                                         H       CF.sub.3 2-OCH.sub.3                                    CON(CH.sub.3).sub.2                                                                         H       OC.sub.2 H.sub.5                                                                       2-SCH.sub.3                                    CON(CH.sub.3).sub.2                                                                         H       OC.sub.2 H.sub.5                                                                       3-OCF.sub.3                                    CON(CH.sub.3)OCH.sub.3                                                                      H       CH.sub.3 2-OCH.sub.3                                    CON(CH.sub.3)OCH.sub.3                                                                      H       OCH.sub.3                                                                              3-OCH.sub.3                                    CON(CH.sub.3)OCH.sub.3                                                                      H       Cl       2-OCH.sub.3                                    CO.sub.2 (CH.sub.2).sub.2 Cl                                                                H       Cl       2-N(CH.sub.3).sub.2                            CO.sub.2 (CH.sub.2).sub.2 OCH.sub.3                                                         H       Cl       2-CN                                           CO.sub.2 (CH.sub.2).sub.2 OC.sub.2 H.sub.5                                                  CH.sub.3                                                                              Cl       2-NO.sub.2                                     CO.sub.2 (CH.sub.2).sub.2 OCF.sub.3                                                         H       Cl       2,3-Cl,Cl                                      OCH.sub.3     H       Cl       2-Cl                                           OCH.sub.3     H       Cl       3-NO.sub.2                                     OC.sub.2 H.sub.5                                                                            H       Cl       4-CN                                           O(CH.sub.2).sub.2 Cl                                                                        H       CH.sub.3 3-CH.sub.3                                     O(CH.sub.2).sub.2 F                                                                         CH.sub.3                                                                              CH.sub. 3                                                                              2-Cl,4-CF.sub.3                                O(CH.sub.2).sub.2 OCH.sub.3                                                                 CH.sub.3                                                                              CH.sub.3 2,3,5-Cl,Cl,Cl                                 O(CH.sub.2).sub.2 OCH.sub.3                                                                 CH.sub.3                                                                              CH.sub.3 3-N(CH.sub.3).sub.2                            O(CH.sub.2).sub.2 SCH.sub.3                                                                 CH.sub.3                                                                              CH.sub.3 4-OCH.sub.3                                    O(CH.sub.2).sub.2 SCH.sub.3                                                                 CH.sub.3                                                                              OCH.sub.3                                                                              2,4-Cl,Cl                                      O(CH.sub.2).sub.2 SCF.sub.3                                                                 CH.sub.3                                                                              OCH.sub.3                                                                              2-OCH.sub.3                                    ______________________________________                                    

                  TABLE C                                                         ______________________________________                                         ##STR8##                                                                     R.sup.1    R.sup.4  R.sup.2   (R.sup.3).sub.m                                 ______________________________________                                        CO.sub.2 CH.sub.3                                                                        H        Cl        H                                               CO.sub.2 CH.sub.3                                                                        H        Cl        3-CH.sub.3                                      CO.sub.2 CH.sub.3                                                                        H        Cl        3-OCH.sub.3                                     CO.sub.2 CH.sub.3                                                                        H        Cl        3-CF.sub.3                                      CO.sub.2 CH.sub.3                                                                        H        Cl        2-F                                             CO.sub.2 CH.sub.3                                                                        H        Cl        2-Cl                                            CO.sub.2 CH.sub.3                                                                        H        Cl        3-Cl                                            CO.sub.2 CH.sub.3                                                                        H        Cl        3-NO.sub.2                                      CO.sub.2 CH.sub.3                                                                        H        Cl        4-NO.sub.2                                      CO.sub.2 CH.sub.3                                                                        H        Cl        2-CN                                            CO.sub.2 CH.sub.3                                                                        H        Cl        2,6-OCH.sub.3,OCH.sub.3                         CO.sub.2 CH.sub.3                                                                        H        Cl        2,4,6-Cl,Cl,Cl                                  CO.sub.2 CH.sub.3                                                                        H        Cl        2-Cl,4-CF.sub.3                                 CO.sub.2 CH.sub.3                                                                        H        Cl        3-N(CH.sub.3).sub.2                             CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        H                                               CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        3-CH.sub.3                                      CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        3-OCH.sub.3                                     CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        3-CF.sub.3                                      CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        2-F                                             CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        2-Cl                                            CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        3-Cl                                            CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        3-NO.sub.2                                      CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        4-NO.sub.2                                      CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        2-CN                                            CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        2,6-OCH.sub.3,OCH.sub.3                         CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        2,4,6-Cl,Cl,Cl                                  CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        2-Cl,4-CF.sub.3                                 CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        3-N(CH.sub.3).sub.2                             CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  H                                               CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  3-CH.sub.3                                      CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  3-OCH.sub.3                                     CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  3-CF.sub.3                                      CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  2-F                                             CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  2-Cl                                            CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  3-Cl                                            CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  3-NO.sub.2                                      CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  4-NO.sub.2                                      CO.sub. 2 CH.sub.3                                                                       H        CH.sub.3  2-CN                                            CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  2,6-OCH.sub.3,OCH.sub.3                         CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  2,4,6-Cl,Cl,Cl                                  CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  2-Cl,4-CF.sub.3                                 CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  3-N(CH.sub.3).sub.2                             CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  H                                               CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  3-CH.sub.3                                      CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  3-OCH.sub.3                                     CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  3-CF.sub.3                                      CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  2-F                                             CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  2-Cl                                            CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  3-Cl                                            CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  3-NO.sub.2                                      CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  4-NO.sub.2                                      CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  2-CN                                            CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  2,6-OCH.sub.3,OCH.sub.3                         CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  2,4,6-Cl,Cl,Cl                                  CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  2-Cl,4-CF.sub.3                                 CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  3-N(CH.sub.3).sub.2                             CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 H                                               CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 3-CH.sub.3                                      CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 3-OCH.sub.3                                     CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 3-CF.sub.3                                      CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 2-F                                             CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 2-Cl                                            CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 3-Cl                                            CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 3-NO.sub.2                                      CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 4-NO.sub.2                                      CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 2-CN                                            CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 2,6-OCH.sub.3,OCH.sub.3                         CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 2,4,6-Cl,Cl,Cl                                  CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 2-Cl,4-CF.sub.3                                 CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 3-N(CH.sub.3).sub.2                             Cl         H        Cl        H                                               Cl         H        Cl        3-CH.sub.3                                      Cl         H        Cl        3-OCH.sub.3                                     Cl         H        Cl        3-CF.sub.3                                      Cl         H        Cl        2-F                                             Cl         H        Cl        2-Cl                                            Cl         H        Cl        3-Cl                                            Cl         H        Cl        3-NO.sub.2                                      Cl         H        Cl        4-NO.sub.2                                      Cl         H        Cl        2-CN                                            Cl         H        Cl        2,6-OCH.sub.3,OCH.sub.3                         Cl         H        Cl        2,4,6-Cl,Cl,Cl                                  Cl         H        Cl        2-Cl,4-CF.sub.3                                 Cl         H        Cl        3-N(CH.sub.3).sub.2                             Cl         CH.sub.3 Cl        H                                               Cl         CH.sub.3 Cl        3-CH.sub.3                                      Cl         CH.sub.3 Cl        3-OCH.sub.3                                     Cl         CH.sub.3 Cl        3-CF.sub.3                                      Cl         CH.sub.3 Cl        2-F                                             Cl         CH.sub.3 Cl        2-Cl                                            Cl         CH.sub.3 Cl        3-Cl                                            Cl         CH.sub.3 Cl        3-NO.sub.2                                      Cl         CH.sub.3 Cl        4-NO.sub.2                                      Cl         CH.sub.3 Cl        2-CN                                            Cl         CH.sub.3 Cl        2,6-OCH.sub.3,OCH.sub.3                         Cl         CH.sub.3 Cl        2,4,6-Cl,Cl,Cl                                  Cl         CH.sub.3 Cl        2-Cl,4-CF.sub.3                                 Cl         CH.sub.3 Cl        3-N(CH.sub.3).sub.2                             Cl         H        CH.sub.3  H                                               Cl         H        CH.sub.3  3-CH.sub.3                                      Cl         H        CH.sub.3  3-OCH.sub.3                                     Cl         H        CH.sub.3  3-CF.sub.3                                      Cl         H        CH.sub.3  2-F                                             Cl         H        CH.sub.3  2-Cl                                            Cl         H        CH.sub.3  3-Cl                                            Cl         H        CH.sub.3  3-NO.sub.2                                      Cl         H        CH.sub.3  4-NO.sub.2                                      Cl         H        CH.sub.3  2-CN                                            Cl         H        CH.sub.3  2,6-OCH.sub.3,OCH.sub.3                         Cl         H        CH.sub.3  2,4,6-Cl,Cl,Cl                                  Cl         H        CH.sub.3  2-Cl,4-CF.sub.3                                 Cl         H        CH.sub.3  3-N(CH.sub.3).sub.2                             Cl         H        CF.sub.3  H                                               Cl         H        CF.sub.3  3-CH.sub.3                                      Cl         H        CF.sub.3  3-OCH.sub.3                                     Cl         H        CF.sub.3  3-CF.sub.3                                      Cl         H        CF.sub.3  2-F                                             Cl         H        CF.sub.3  2-Cl                                            Cl         H        CF.sub.3  3-Cl                                            Cl         H        CF.sub.3  3-NO.sub.2                                      Cl         H        CF.sub.3  4-NO.sub.2                                      Cl         H        CF.sub.3  2-CN                                            Cl         H        CF.sub.3  2,6-OCH.sub.3,OCH.sub.3                         Cl         H        CF.sub.3  2,4,6-Cl,Cl,Cl                                  Cl         H        CF.sub.3  2-Cl,4-CF.sub.3                                 Cl         H        CF.sub.3  3-N(CH.sub.3).sub.2                             Cl         H        OCH.sub.3 H                                               Cl         H        OCH.sub.3 3-CH.sub.3                                      Cl         H        OCH.sub.3 3-OCH.sub.3                                     Cl         H        OCH.sub.3 3-CF.sub.3                                      Cl         H        OCH.sub.3 2-F                                             Cl         H        OCH.sub.3 2-Cl                                            Cl         H        OCH.sub.3 3-Cl                                            Cl         H        OCH.sub.3 3-NO.sub.2                                      Cl         H        OCH.sub.3 4-NO.sub.2                                      Cl         H        OCH.sub.3 2-CN                                            Cl         H        OCH.sub.3 2,6-OCH.sub.3,OCH.sub.3                         Cl         H        OCH.sub.3 2,4,6-Cl,Cl,Cl                                  Cl         H        OCH.sub.3 2-Cl,4-CF.sub.3                                 Cl         H        OCH.sub.3 3-N(CH.sub.3).sub.2                             ______________________________________                                    

                  TABLE D                                                         ______________________________________                                         ##STR9##                                                                     R.sup.1    R.sup.4  R.sup.2   (R.sup.3).sub.m                                 ______________________________________                                        CO.sub.2 CH.sub.3                                                                        H        Cl        H                                               CO.sub.2 CH.sub.3                                                                        H        Cl        3-CH.sub.3                                      CO.sub.2 CH.sub.3                                                                        H        Cl        3-OCH.sub.3                                     CO.sub.2 CH.sub.3                                                                        H        Cl        3-CF.sub.3                                      CO.sub.2 CH.sub.3                                                                        H        Cl        2-F                                             CO.sub.2 CH.sub.3                                                                        H        Cl        2-Cl                                            CO.sub.2 CH.sub.3                                                                        H        Cl        3-Cl                                            CO.sub.2 CH.sub.3                                                                        H        Cl        3-NO.sub.2                                      CO.sub.2 CH.sub.3                                                                        H        Cl        4-NO.sub.2                                      CO.sub.2 CH.sub.3                                                                        H        Cl        2-CN                                            CO.sub.2 CH.sub.3                                                                        H        Cl        2,6-OCH.sub.3,OCH.sub.3                         CO.sub.2 CH.sub.3                                                                        H        Cl        2,4,6-Cl,Cl,Cl                                  CO.sub.2 CH.sub.3                                                                        H        Cl        2-Cl,4-CF.sub.3                                 CO.sub.2 CH.sub.3                                                                        H        Cl        3-N(CH.sub.3).sub.2                             CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        H                                               CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        3-CH.sub.3                                      CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        3-OCH.sub.3                                     CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        3-CF.sub.3                                      CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        2-F                                             CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        2-Cl                                            CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        3-Cl                                            CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        3-NO.sub.2                                      CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        4-NO.sub.2                                      CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        2-CN                                            CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        2,6-OCH.sub.3,OCH.sub.3                         CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        2,4,6-Cl,Cl,Cl                                  CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        2-Cl,4-CF.sub.3                                 CO.sub.2 CH.sub.3                                                                        CH.sub.3 Cl        3-N(CH.sub.3).sub.2                             CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  H                                               CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  3-CH.sub.3                                      CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  3-OCH.sub.3                                     CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  3-CF.sub.3                                      CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  2-F                                             CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  2-Cl                                            CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  3-Cl                                            CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  3-NO.sub.2                                      CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  4-NO.sub.2                                      CO.sub. 2 CH.sub.3                                                                       H        CH.sub.3  2-CN                                            CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  2,6-OCH.sub.3,OCH.sub.3                         CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  2,4,6-Cl,Cl,Cl                                  CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  2-Cl,4-CF.sub.3                                 CO.sub.2 CH.sub.3                                                                        H        CH.sub.3  3-N(CH.sub.3).sub.2                             CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  H                                               CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  3-CH.sub.3                                      CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  3-OCH.sub.3                                     CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  3-CF.sub.3                                      CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  2-F                                             CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  2-Cl                                            CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  3-Cl                                            CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  3-NO.sub.2                                      CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  4-NO.sub.2                                      CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  2-CN                                            CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  2,6-OCH.sub.3,OCH.sub.3                         CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  2,4,6-Cl,Cl,Cl                                  CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  2-Cl,4-CF.sub.3                                 CO.sub.2 CH.sub.3                                                                        H        CF.sub.3  3-N(CH.sub.3).sub.2                             CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 H                                               CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 3-CH.sub.3                                      CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 3-OCH.sub.3                                     CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 3-CF.sub.3                                      CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 2-F                                             CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 2-Cl                                            CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 3-Cl                                            CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 3-NO.sub.2                                      CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 4-NO.sub.2                                      CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 2-CN                                            CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 2,6-OCH.sub.3,OCH.sub.3                         CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 2,4,6-Cl,Cl,Cl                                  CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 2-Cl,4-CF.sub.3                                 CO.sub.2 CH.sub.3                                                                        H        OCH.sub.3 3-N(CH.sub.3).sub.2                             Cl         H        Cl        H                                               Cl         H        Cl        3-CH.sub.3                                      Cl         H        Cl        3-OCH.sub.3                                     Cl         H        Cl        3-CF.sub.3                                      Cl         H        Cl        2-F                                             Cl         H        Cl        2-Cl                                            Cl         H        Cl        3-Cl                                            Cl         H        Cl        3-NO.sub.2                                      Cl         H        Cl        4-NO.sub.2                                      Cl         H        Cl        2-CN                                            Cl         H        Cl        2,6-OCH.sub.3,OCH.sub.3                         Cl         H        Cl        2,4,6-Cl,Cl,Cl                                  Cl         H        Cl        2-Cl,4-CF.sub.3                                 Cl         H        Cl        3-N(CH.sub.3).sub.2                             Cl         CH.sub.3 Cl        H                                               Cl         CH.sub.3 Cl        3-CH.sub.3                                      Cl         CH.sub.3 Cl        3-OCH.sub.3                                     Cl         CH.sub.3 Cl        3-CF.sub.3                                      Cl         CH.sub.3 Cl        2-F                                             Cl         CH.sub.3 Cl        2-Cl                                            Cl         CH.sub.3 Cl        3-Cl                                            Cl         CH.sub.3 Cl        3-NO.sub.2                                      Cl         CH.sub.3 Cl        4-NO.sub.2                                      Cl         CH.sub.3 Cl        2-CN                                            Cl         CH.sub.3 Cl        2,6-OCH.sub.3,OCH.sub.3                         Cl         CH.sub.3 Cl        2,4,6-Cl,Cl,Cl                                  Cl         CH.sub.3 Cl        2-Cl,4-CF.sub.3                                 Cl         CH.sub.3 Cl        3-N(CH.sub.3).sub.2                             Cl         H        CH.sub.3  H                                               Cl         H        CH.sub.3  3-CH.sub.3                                      Cl         H        CH.sub.3  3-OCH.sub.3                                     Cl         H        CH.sub.3  3-CF.sub.3                                      Cl         H        CH.sub.3  2-F                                             Cl         H        CH.sub.3  2-Cl                                            Cl         H        CH.sub.3  3-Cl                                            Cl         H        CH.sub.3  3-NO.sub.2                                      Cl         H        CH.sub.3  4-NO.sub.2                                      Cl         H        CH.sub.3  2-CN                                            Cl         H        CH.sub.3  2,6-OCH.sub.3,OCH.sub.3                         Cl         H        CH.sub.3  2,4,6-Cl,Cl,Cl                                  Cl         H        CH.sub.3  2-Cl,4-CF.sub.3                                 Cl         H        CH.sub.3  3-N(CH.sub.3).sub.2                             Cl         H        CF.sub.3  H                                               Cl         H        CF.sub.3  3-CH.sub.3                                      Cl         H        CF.sub.3  3-OCH.sub.3                                     Cl         H        CF.sub.3  3-CF.sub.3                                      Cl         H        CF.sub.3  2-F                                             Cl         H        CF.sub.3  2-Cl                                            Cl         H        CF.sub.3  3-Cl                                            Cl         H        CF.sub.3  3-NO.sub.2                                      Cl         H        CF.sub.3  4-NO.sub.2                                      Cl         H        CF.sub.3  2-CN                                            Cl         H        CF.sub.3  2,6-OCH.sub.3,OCH.sub.3                         Cl         H        CF.sub.3  2,4,6-Cl,Cl,Cl                                  Cl         H        CF.sub.3  2-Cl,4-CF.sub.3                                 Cl         H        CF.sub.3  3-N(CH.sub.3).sub.2                             Cl         H        OCH.sub.3 H                                               Cl         H        OCH.sub.3 3-CH.sub.3                                      Cl         H        OCH.sub.3 3-OCH.sub.3                                     Cl         H        OCH.sub.3 3-CF.sub.3                                      Cl         H        OCH.sub.3 2-F                                             Cl         H        OCH.sub.3 2-Cl                                            Cl         H        OCH.sub.3 3-Cl                                            Cl         H        OCH.sub.3 3-NO.sub.2                                      Cl         H        OCH.sub.3 4-NO.sub.2                                      Cl         H        OCH.sub.3 2-CN                                            Cl         H        OCH.sub.3 2,6-OCH.sub.3,OCH.sub.3                         Cl         H        OCH.sub.3 2,4,6-Cl,Cl,Cl                                  Cl         H        OCH.sub.3 2-Cl,4-CF.sub.3                                 Cl         H        OCH.sub.3 3-N(CH.sub.3).sub.2                             ______________________________________                                    

The substituted sulfonylureas I, and herbicidal agents containing them,may be applied for instance in the form of directly sprayable solutions,powders, suspensions (including high-percentage aqueous, oily or othersuspensions), dispersions, emulsions, oil dispersions, pastes, dusts,broadcasting agents, or granules by spraying, atomizing, dusting,broadcasting or watering. The forms of application depend entirley onthe purpose for which the agents are being used, but they must ensure asfine a distribution of the active ingredients according to the inventionas possible.

For the preparation of solutions, emulsions, pastes and oil dispersionsto be sprayed direct, mineral oil fractions of medium to high boilingpoint, such as kerosene or diesel oil, further coal-tar oils, and oilsof vegetable or animal origin, aliphatic, cyclic and aromatichydrocarbons such as benzene, toluene, xylene, paraffin,tetrahydronaphtalene, alkylated naphthalenes and their derivatives suchas methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone,chlorobenzene, isophorone, etc., and strongly polar solvents such asN,N-dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water,etc. are suitable.

Aqueous formulations may be prepared from emulsion concentrates, pastes,oil dispersions or wettable powders by adding water. To prepareemulsions, pastes and oil dispersions the ingredients as such ordissolved in an oil or solvent may be homogenized in water by means ordisperesing agents, adherents or emulsifiers. Concentrates which aresuitable for dilution with water may be prepared from active ingredient,wetting agent, adherent, emulsifying or dispersing agent and possiblysolvent oil.

Examples of surfactants are: alkali metal, alkaline earth metal andammonium salts of aromatic sulfonic acids, e.g., ligninsulfonic acid,phenolsulfonic acid, naphthalenesulfonic acid anddibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, and alkyl, lauryl ether and fatty alcohol sulfates, alkalimetal and alkaline earth metal salts of dibutylnaphthalenesulfonic acid,lauryl ether sulfate, fatty alcohol sulfates, and salts of sulfatedhexadecanols, heptadecanols, and octadecanols, salts of fatty alcoholglycol ethers, condensation products of sulfonated naphthalene andnaphthalene derivatives with formaldehyde, condensation products ofnaphthalene or naphthalenesulfonic acids with phenol and formaldehyde,polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol,ethoxylated octylphenol and ethoxylated nonylphenol, alkylphenolpolyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyetheralcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylatedpolyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitolesters, lignin-sulfite waste liquors and methyl cellulose. powders,dusts and broadcasting agents may be prepared by mixing or grinding theactive ingredients with a solid carrier.

Granules, e.g., coated, impregnated or homogeneous granules, may beprepared by bonding the active ingredients to solid carriers. Examplesof solid carriers are mineral earths such as silicic acids, silica gels,silicates, talc, kaolin, attapulgus clay, limestone, lime, chalk, bole,loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesiumsulfate, magnesium oxide, ground plastics, fertilizers such as ammoniumsulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetableproducts such as grain meals, bark meal, wood meal, and nutshell meal,cellulosic powders, etc.

The formulations contain from 0.1 to 95, and preferably 0.5 to 90, % byweight of active ingredient.

Examples of formulations are as follows:

2. 90 parts by weight of compound no. 1.002 is mixed with 10 parts byweight of N-methyl-alpha-pyrrolidone. A mixture is obtained which issuitable for application in the form of very fine drops.

II. 20 parts by weight of compound no. 1.003 is dissolved in a mixtureconsisting of 80 parts by weight of xylene, 10 parts by weight of theadduct of 8 to 10 moles of ethylene oxide and 1 mole of oleicacid-N-monoethanolamide, 5 parts by weight of the calcium salt ofdodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40moles of ethylene oxide and 1 mole of castor oil. By pouring thesolution into 100,000 parts by weight of water and uniformlydistributing it therein, an aqueous dispersion is obtained containing0.2% by weight of the active ingredient.

III. 20 parts by weight of compound no. 1.006 is dissolved in a mixtureconsisting of 40 parts by weight of cyclohexanone, 30 parts by weight ofisobutanol, 20 parts by weight of the adduct of 7 moles of ethyleneoxide and 1 mole of isooctylphenol, and 10 parts by weight of the adductof 40 moles of ethylene oxide and 1 mole of castor oil. By pouring thesolution into 100,000 parts by weight of water and finely distributingit therein, an aqueous dispersion is obtained containing 0.2% by weightof the active ingredient.

IV. 20 parts by weight of compound no. 1.002 is dissolved in a mixtureconsisting of 25 parts by weight of cyclohexanone, 65 parts by weight ofa mineral oil fraction having a boiling point between 210 20 and 280 °C., and 10 parts by weight of the adduct of 40 moles of ethylene oxideand 1 mole of castor oil. By pouring the solution into 100,000 parts byweight of water and uniformly distributing it therein, an aqueousdispersion is obtained containing 0.2% by weight of the activeingredient.

V. 20 parts by weight of compound no. 5.005 is well mixed with 3 partsby weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonicacid, 17 parts by weight of the sodium salt of a lignin-sulfonic acidobtained from a sulfite waste liquor, and 60 parts by weight of powderedsilica gel, and triturated in a hammer mill. By uniformly distributingthe mixture in 20,000 parts by weight of water, a spray liquor isobtained containing 0.1% by weight of the active ingredient.

VI. 3 parts by weight of compound no. 1.006 is intimately mixed with 97parts by weight of particulate kaolin. A dust is obtained containing 3 %byweight of the active ingredient.

VII. 30 parts by weight of compound no. 5.005 is intimately mixed with amixture consisting of 92 parts by weight of powdered silica gel and 8parts by weight of paraffin oil which has been sprayed onto the surfaceof this silica gel. A formulation of the active ingredient is obtainedhaving good adherence.

VIII. 20 parts by weight of compound no. 6.003 is intimately mixed with2 parts of the calcium salt of dodecylbenzenesulfonic acid, 8 parts of afatty alcohol polyglycol ether, 2 parts of the sodium salt of aphenolsulfonic acid-urea-formaldehyde condensate and 68 parts of aparaffinic mineral oil. A stable oily dispersion is obtained.

The active ingredients or the hervicidal agents containing them may beapplied pre- or postemergence. If certain crop plants tolerate theactive ingredients less well, application techniques may be used inwhich the herbicidal agents are sprayed from suitable equipment in sucha manner that the leaves of sensitive crop plants are if possible nottouched, and the agents reach the soil or the unwanted plants growingbeneath the crop plants (post-directed, lay-by treatment).

The application rates depend on the objective to be achieved, the timeof the year, the plants to be combated and their growth stage, and arefrom 0.001 to 3.0, preferably 0.01 to 1.0, kg of active ingredient perhectare.

The sulfonylureas of the general formula I may exercise a variety ofinfluences on practically all plant development stages, and aretherefore used as growth regulators. The diversity of action of growthregulators depends especially on

a) the type and variety of plant;

b) the time applied, with reference to the development stage of theplants and the time of the year;

c) the place and method of application (seed treatment, soil treatment,or application to foliage);

d) climatic factors, e.g., average temperature, amount of precipitate,sunshine and duration;

e) soil conditions (including fertilization);

f) the formulation of the active ingredient; and

g) the concentration at which the active ingredient is applied.

A description of some of the various possibilities of using the growthregulators according to the invention in agriculture and horticulture isgiven below.

A. Vegetative plant growth can be inhibited to a considerable extent, afact which is manifested particularly in a reduction in plant height.The treated plants thus have a compact habit; furthermore, the leafcolor is darker. Of advantage in practice is for example the reductionin grass growth on roadsides, hedges, canal embankments and on areassuch as parks, sportsgrounds, fruit orchards, lawns and airfields, thusreducing expensive and time-consuming mowing.

Cost-intensive pruning can be reduced in fruit and other trees andshrubs as a result of the use of growth regulators.

A further feature of economic interest is the increase in the rigor ofcrops which tend to lodge, such as cereals, Indian corn, sunflowers andsoybeans. The shortening and strengthening of the stem thus causedreduces or eliminates the danger of lodging under unfavorable weatherconditions.

The use of growth regulators is also important for inhibiting plantheight and changing the time of ripening in cotton. It is thus possiblefor this important crop to be harvested completely mechanically.

Growth regulators may also increase or inhibit lateral branching. Thisis of interest when, for instance in tobacco plants, it is desired toinhibit the formation of lateral shoots (suckers) in favor of leafdevelopment.

With growth regulators, it is possible for instance in winter rape toconsiderably increase the resistance to freeze injury. On the one hand,upward growth and the development of a too luxuriant (and thusparticularly frost-susceptible) leaf or plant mass are inhibited; on theother, the young rape plants are kept, in spite of favorable growthconditions, in the vegetative development stage before winter frostsbegin. The danger of freeze injury is thus eliminated in plants whichtend to lose prematurely their inhibition to bloom and pass into thegenerative phase. In other crops, too, e.g., winter cereals, it isadvantages if the plants are well tillered in the fall as a result oftreatment with the compounds according to the invention, but enterwinter with not too lush a growth. This is a preventive measure againstincreased susceptibility to freeze injury and--because of the relativelylow leaf or plant mass--attack by various (especially fungus) diseases.The inhibition of vegetative growth also makes closer planting possiblein numerous crops, which means an increase in yield, based on the areacropped.

B. Better yields both of plant parts and plant materials may be obtainedwith the novel agents. It is thus for instance possible to induceincreased formation of buds, blossom, leaves, fruit, seed grains, rootsand tubers, to increase the sugar content of sugarbeets, sugarcane andcitrus fruit, to raise the protein content of cereals and soybeans, andto stimulate the increased formation of latex in rubber trees.

The sulfonylureas of the formula I may raise the yield by influencingplant metabolism or by promoting or inhibiting vegetative and/orgenerative plant growth.

C. It is also possible with sulfonylureas I to shorten or lengthengrowth stages and to accelerate or retard the ripening process in plantsparts either before or after harvesting.

A factor of economic interest is for example the facilitation ofharvesting made possible by a chemical, temporally concentratedloosening (abscission) of the adherence of stalks to the branches ofcitrus fruit, olive trees, and other kinds of pomes, drupes andindehiscent fruit. The same mechanism, i.e., promotion of the formationof separation layers between fruit or leaf and stem of the plant, isalso essential for a readily controllable defoliation of crop plants. D.Further, transpiration in crop plants may be reduced with thesulfonylureas I. This is particularly important for plants growing inagricultural areas which are expensive toirrigate, e.g., in arid orsemi-arid areas. Irrigation frequency can be reduced by using thecompounds according to the invention, making for lower costs. As aresult of theuse of growth regulators, the water available can be betterutilized, because, inter alia,

the size of the stomata opening is reduced;

a thicker epidermis and cuticle are formed;

penetration of the soil by the roots is improved;

the micro-climate in the stand is favorably influenced by the morecompact growth.

The active-ingredients according to the invention may be applied notonly to the seed (as a disinfectant), but also to the soil, i.le., viathe roots,and to the foliage by spraying.

As a result of the good tolerance of compounds I by crop plants, theapplication rate may vary within wide limits. When the activeingredients are used for treating seed, amounts of from 0.001 to 50, andpreferably from 0.01 to 10, g are generally required. For foliage andsoil treatment, amounts of from 0.01 to 10, and preferably from 0.01 to5, kg/ha are generally considered to be sufficient.

In view of the number of application methods possible, the compoundsaccording to the invention, or agents containing them, may be used in afurther large number of crops for removing unwanted plants.

To increase the spectrum of action and to achieve synergistic effects,the sulfonylureas of the formula I may be mixed and applied togetherwith numerous representatives of other herbicidal or growth-regulatingactive ingredient group. Examples of suitable components are diagines,4H-3,1-benzoxazine derivatives, benzothiadiazinones,2,6-dinitroanilines, N-phenylcarbamats, thiolcarbamates, halocarboxylicacids, triazines, amides, ureas, diphenyl ethers, triazinones, uracils,benzofuran derivatives, cyclohexane-1,3-dione derivatives,quinolinecarboxylic acids, phenyloxy- or heteroaryloxyphenylpropionicacids and derivatives thereof, etc.

It may also be useful to apply the novel compounds of the formula I,either alone or in combination with other hervicides, in admixture withother crop protection agents, e.g., agents for combating pests orphytopathogenic fungi or bacteria. The compounds may also be mixed withsolutions of mineral salts used to remedy nutritional or trace elementdeficiencies. Non-phytotoxic oils and oil concentrates may also beadded.

The directions given in the examples below were used, after appropriatemodifications to the starting compounds, to obtain further compounds ofthe formula I.

SYNTHESIS EXAMPLES 1. Manufacture of Intermediates III ##STR10## 1.12-Amino-6-methyl-4-(2-cyano-1-phenoxy)-pyrimidine ##STR11##

At 600° C. and while stirring, 4.7 g of potassium hydroxide (84 mmol)was added to 10.0 g (84 mmol) of o-hydroxybenzonitrile in 100 ml ofmethanol until a clear solution formed. The reaction mixture wassubsequently evaporated down. The residue was taken up in 100 ml ofN-methyl-2-pyttolidone, 12.0 g (84 mmol) of2-amino-4-chloro-6-methylpyrimidine was added and the mixture stirredfor 6 hours at 140° C. After cooling, the reaction mixture was poured,at 25° C., onto ice and the precipitate was isolated.

There was obtained 90% of theory of the product; m.p. 163°-165° C.

1.2 2-Amino-4-chloro-6-(2,4-dichloro-1-phenoxy)-1,3,5-triazine ##STR12##

7.9 g (48.5 mmol) of 2,4-dichlorophenol and 8.0 g (48.5 mmol) of2-amino-4,6-dichloro-1,3,5-triazine were added to a solution of 5.1 g(48.5 mmol) of sodium carbonate and 150 ml of water, and the mixture wasstirred for 4 hours at 50° C. After the mixture had cooled to 25° C. theprecipitate was filtered off and dried; there was obtained 92% of theoryof the product.

¹ H NMR data (DMSO, int. TMS, 250 MHz): δ8.32 (broad; NH), 8.24 (broad;NH); 7.83, 7.53 ppm (multiplets, aromatic protons).

The compounds given in the table below were obtained analogously.

    __________________________________________________________________________     ##STR13##                                                                                                  Melting point (°C.) or the                                             .sup.1 H NMR shift (δ/ppm) of the                                       H(5) proton on the pyridine                     No. R.sup.2                                                                           Z  X  (R.sup.3).sub.m ring (vs TMS)                                   __________________________________________________________________________    1.3 Cl  CH O  2-OCH.sub.3     188-190                                         1.4 Cl  CH O  3-OCH.sub.3     140-142                                         1.5 Cl  CH O  4-OCH.sub.3     6.13(d.sub.6 -DMSO)                             1.6 Cl  CH O  2-Cl            155-158                                         1.7 Cl  CH O  3-Cl            140-141                                         1.8 Cl  CH O  2-NO.sub.2      6.48(d.sub.6 -DMSO)                             1.9 Cl  CH O  3-NO.sub.2      6.40(d.sub.6 -DMSO)                             1.10                                                                              Cl  CH O  4-NO.sub.2      6.43(d.sub.6 -DMSO)                             1.11                                                                              Cl  CH O  2-CN            6.53(d.sub.6 -DMSO)                             1.12                                                                              Cl  CH O  3-CN            204-205                                         1.13                                                                              Cl  CH O  4-CN            6.37(d.sub.6 -DMSO)                             1.14                                                                              Cl  CH O  2-F             160-165                                         1.15                                                                              Cl  CH O  3-CF.sub.3      6.25(CDCl.sub.3)                                1.16                                                                              Cl  CH O  2-OCH.sub.3, 6-OCH.sub.3                                                                      188-190                                         1.17                                                                              Cl  CH O  2-Cl, 4-Cl, 6-Cl                                                                              6.36(d.sub.6 -DMSO)                             1.18                                                                              CH.sub.3                                                                          CH O  3-OCH.sub.3     194-195                                         1.19                                                                              CH.sub.3                                                                          CH O  4-OCH.sub.3     5.92(CDCl.sub.3)                                1.20                                                                              CH.sub.3                                                                          CH O  3-CN            119-120                                         1.21                                                                              CH.sub.3                                                                          CH O  4-CN            215-217                                         1.22                                                                              CH.sub.3                                                                          CH O  3-CF.sub.3      6.07(CDCl.sub.3)                                1.23                                                                              CH.sub.3                                                                          CH O  2-F             6.13(d.sub.6 -DMSO)                             1.24                                                                              CH.sub.3                                                                          CH O  2-NO.sub.2      6.20(d.sub.6 -DMSO)                             1.25                                                                              CH.sub.3                                                                          CH O  3-NO.sub.2      179-180                                         1.26                                                                              CH.sub.3                                                                          CH O  4-NO.sub.2      219-220                                         1.27                                                                              CH.sub.3                                                                          CH O  2-Cl            183-184                                         1.28                                                                              CH.sub.3                                                                          CH O  3-Cl            159-160                                         1.29                                                                              CH.sub.3                                                                          CH O  4-Cl            219-220                                         1.30                                                                              CH.sub.3                                                                          CH O  2-OCH.sub.3, 6-OCH.sub.3                                                                      168-173                                         1.31                                                                              CH.sub.3                                                                          CH O  2-Cl, 4-Cl, 6-Cl                                                                              130-131                                         1.32                                                                              OCH.sub.3                                                                         CH O  4-OCH.sub.3     5.36(CDCl.sub.3)                                1.33                                                                              Cl  CH S  2-Cl            6.04(CDCl.sub.3)                                1.34                                                                              Cl  CH S  2-OCH.sub.3     5.74(d.sub.6 -DMSO)                             1.35                                                                              Cl  N  O  2-OCH.sub.3     230                                             1.36                                                                              Cl  N  O  3-OCH.sub.3     3.76[(OCH.sub.3)d.sub.6 -DMSO]                  1.37                                                                              Cl  N  O  4-OCH.sub.3     230                                             1.38                                                                              Cl  N  O  2-Cl            220-223                                         1.39                                                                              Cl  N  O  3-Cl            227-228                                         1.40                                                                              Cl  N  O  4-Cl            >230                                            1.41                                                                              Cl  N  O  2-CN            >230                                            1.42                                                                              Cl  N  O  3-CN            >230                                            1.43                                                                              Cl  N  O  4-CN            >230                                            1.44                                                                              Cl  CH O  2-Cl, 4-Cl      6,43(d.sub.6 -DMSO)                             1.45                                                                              Cl  CH O  2-Cl, 4-CF.sub.3                                                                              104-106                                         1.46                                                                              Cl  CH O  3-N(CH.sub.3).sub.2                                                                           194-204                                         1.47                                                                              CH.sub.3                                                                          CH O  3-N(CH.sub.3).sub.2                                                                           232-235                                         1.48                                                                              OCH.sub.3                                                                         CH O  2-Cl            5.53(d.sub.6 -DMSO)                             1.49                                                                              OCH.sub.3                                                                         CH O  3-Cl            112-115                                         1.50                                                                              OCH.sub.3                                                                         CH O  4-Cl            105-108                                         1.51                                                                              OCH.sub.3                                                                         CH O  2-OCH.sub.3     104-106                                         1.52                                                                              OCH.sub.3                                                                         CH O  3-OCH.sub.3     85-88                                           1.53                                                                              CH.sub.3                                                                          CH S  4-OCH.sub.3     200-203                                         1.54                                                                              F   CH O  2-OCH.sub.3     166                                             1.55                                                                              F   CH O  3-OCH.sub.3     115-116                                         1.56                                                                              F   CH O  4-OCH.sub.3     195-197                                         1.57                                                                              OCH.sub.3                                                                         CH O  3-OCH.sub.3, 4-OCH.sub.3, 5-OCH.sub.3                                                         120-122                                         1.58                                                                              OCH.sub.3                                                                         CH O  4-OC.sub.2 H.sub.5                                                                            145-146                                         1.59                                                                              OC.sub.2 H.sub.5                                                                  CH O  2-OCH.sub.3     130-131                                         1.60                                                                              OC.sub.2 H.sub.5                                                                  CH O  4-OC.sub.2 H.sub.5                                                                            127                                             1.61                                                                              CF.sub.3                                                                          CH O  2-OCH.sub.3     168-170                                         1.62                                                                              CF.sub.3                                                                          CH O  3-OCH.sub.3     127-129                                         1.63                                                                              OC.sub.2 H.sub.5                                                                  CH O  3-OCH.sub.3      82                                             1.64                                                                              OCH.sub.3                                                                         CH O  3-OCH.sub.3, 5-OCH.sub.3                                                                      85-86                                           1.65                                                                              OCH.sub.3                                                                         CH O  3-OCH.sub.3, 4-OCH.sub.3                                                                      148-149                                         1.66                                                                              CF.sub.3                                                                          CH O  3-N(CH.sub.3).sub.2                                                                           115-116                                         1.67                                                                              OC.sub.2 H.sub.5                                                                  CH O  3-N(CH.sub.3).sub.2                                                                           122-124                                         1.68                                                                              OCH.sub.3                                                                         CH O  2-OCH.sub.3, 3-OCH.sub.3                                                                      5,42(CDCl.sub.3)                                1.69                                                                              OCH.sub.3                                                                         CH O  3,4-(OCH.sub.2 O)                                                                             135-140                                         1.70                                                                              OCH.sub.3                                                                         CH O  2-OC.sub.2 H.sub.5                                                                            5,40(CDCl.sub.3)                                1.71                                                                              OCH.sub.3                                                                         CH O  2-OCH.sub.3, 4-CH.sub.3                                                                       5,38(CDCl.sub.3)                                1.72                                                                              OCH.sub.3                                                                         CH O  2-OCH.sub.3, 4-(E)-CHCHCH.sub.3                                                               5,39(CDCl.sub.3)                                1.73                                                                              OCH.sub.3                                                                         CH O  2-OCH.sub.2 C.sub.6 H.sub.5                                                                   75-78                                           1.74                                                                              OCH.sub.3                                                                         CH O  4-OCH.sub. 2 C.sub.6 H.sub.5                                                                  152-155                                         1.75                                                                              Cl  CH O  2-CO.sub.2 CH.sub.3                                                                           200-201                                         1.76                                                                              OCH.sub.3                                                                         CH O  2-t.-C.sub.4 H.sub.9, 4-OCH.sub.3                                                             135-138                                         1.77                                                                              OCH.sub.3                                                                         CH O                                                                                 ##STR14##      117-125                                         1.78                                                                              OCH.sub.3                                                                         CH O                                                                                 ##STR15##      174-180                                         1.79                                                                              OCH.sub.3                                                                         CH O  3-CH.sub.3, 4-SCH.sub.3                                                                       96-98                                           1.80                                                                              OCH.sub.3                                                                         CH O  2-Cl, 4-OCH.sub.3                                                                             5,45(d.sub.6 -DMSO)                             1.81                                                                              OCH.sub.3                                                                         CH O  4-SCH.sub.3     5,43(d.sub.6 -DMSO)                             1.82                                                                              OCH.sub.3                                                                         CH O  2-CH.sub.3, 4-SCH.sub.3                                                                       5.39(CDCl.sub.3)                                1.83                                                                              OCH.sub.3                                                                         CH O  2-OCH.sub.3, 4-C(O)CH.sub.3                                                                   5.49(CDCl.sub.3)                                1.84                                                                              OCH.sub.3                                                                         CH O  2-OC.sub.2 H.sub.5, 4-Cl                                                                      5.42(d.sub.6 -DMSO)                             __________________________________________________________________________

2. Manufacture of the Intermediates V ##STR16## 2.1 Methyl2-aminosulfonyl-6-chlorobenzoate ##STR17## a)4-Chloro-1,2-benzisothiazol-3-one-1,1-dioxide

504 g (2.02 mol) of methyl 6-chloro-2-aminosulfonylbenzoate was added inportions to a solution of 80 g (2.0 mol) of sodium hydroxide in 2.5liters of water; the temperature rose from 25° C. to 50° C. After 30minutes at this temperature, the mixture was cooled to 25° C. andextracted with methyl tert-butyl ether, and the aqueous phase wasstirred into 2N hydrochloric acid. The precipitate was isolated, washedwith water and dried. There was obtained 330 g (75.8% of theory) of thetitle compound, m.p.: 210°-212° C.

b) Methyl 2-aminosulfonyl-6-chlorobenzoate

93 g (0.43 mmol) of 4-chloro-1,2-benzisothiazol-3-one-1,1-dioxide wassuspended in 0.8 liter of methanol; while gassing with hydrogen chloridethe mixture was refluxed for 3 hours. After cooling to 20° C., suctionfiltration and drying, there was obtained 56% of theory of the titlecompound of m.p. 152°-153° C. By evaporation down the filtrate underreduced pressure and triturating the residue with methyl tert-butylether, renewed filtration and drying there was obtained 39% of theory ofa second fraction of this compound of m.p. 144°-149° C.

For instance the following compounds were obtained analogously:

    ______________________________________                                                  ##STR18##                                                                                    ##STR19##                                            R        mp (°C.)                                                                              mp (°C.)                                       ______________________________________                                        C.sub.2 H.sub.5                                                                         97-101        129-131                                               n-C.sub.3 H.sub.7                                                                      111-113        104-107                                               i-C.sub.3 H.sub.7                                                                      145-147         84-87                                                ______________________________________                                    

2.2 Methyl 2-aminosulfonyl-6-fluorobenzoate ##STR20## a) Methyl2-chlorosulfonyl-6-fluorobenzoate

At 5° C. and while stirring, 108 g (0.64 mol) of methyl6-fluoroanthranilate and 45 g (0.65 mol) of sodium nitrite in 106 ml ofwater were added separately but simultaneously over a period of 1 hourin such a manner to 250 ml of concentrated hydrochloric acid that theester component was in an excess. After the reaction mixture had beenstirred for 20 minutes at 5° to 8° C., it was poured all at once into aprepared solution of 53 g of sulfur dioxide, 1.7 g of copper(II)chloride in a small amount of water and 200 ml of 1,2-dichloroethane,and stirred for a further 10 minutes. The mixture was heated slowly to50° C. and stirred for ninety minutes while passing in 46 g of sulfurdioxide. The mixture was then cooled to 20° C. and 5.5 g of chlorine waspassed in over a 20-minute period while stirring. The organic phase wasthen separated, washed with water and dried. There was obtained 65% oftheory of the title compound as a brownish oil.

b) Methyl 2-aminosulfonyl-6-fluorobenzoate

At 20° to 28° C. and while stirring, 42.5 g of ammonia was gassed into amixture of 252.6 g (1 mol) of methyl 2-chlorosulfonyl-6-fluorobenzoatein 700 ml of anhydrous tetrahydrofuran. After the mixture had beenstirred for an hour at 25° C., the precipitate was filtered off,dissolved in water, and extracted once with ethyl acetate. Acidificationof the aqueous phase with concentrated hydrochloric acid gave 4% oftheory of 4-fluoro-1,2-benzisothiazol-3-one-1,1-dioxide of m.p. 210° to212° C.

The tetrahydrofuran filtrate was concentrated, washed with water,filtered, washed with diethyl ether, filtered again and dried. There wasobtained 80% of theory of the title compound; m.p. 155° to 159° C.

3. Manufacture of Active Ingredients I 3.1 Methyl2-[[[4-chloro-6-[(3-methoxy)-1-phenoxy]pyrimidin-2-yl]aminocarbonyl]aminosulfonyl]benzoate##STR21##

At 25° C., a solution of 6.9 g (29 mmol) of methyl 2-isocyanatosulfonylbenzoate in 40 ml of acetonitrile was added to a suspension of 6.0 g (24mmol) of 2-amino-4-chloro-6-[(3-methoxy)-1-phenoxy]pyrimidine (1.4) in70 ml of acetonitrile. After the mixture had been stirred for 8 hours at70° C. 300 ml of methylene chloride was added and the mixture waswashed, dried and evaporated down at 25° C. The crude product obtainedwas recrystallized from toluene/isopropanol and washed with diethylether. There was obtained 28% theory of the title compound; m.p.152°-154° C. (active ingredient example 1.003). The yield can beincreased by further processing of the mother liquor and the wash phase.

3.2 Methyl2-[[[4-chloro-6-(3-chloro-1-phenoxy)pyrimidin-2-yl]aminocarbonyl]aminosulfonyl]benzoate##STR22##

At room temperature, 7.2 g (30 mmol) of methyl2-isocyanatosulfonylbenzoate was added to a suspension of 7.0 g (27mmol) of 2-amino-4-chloro-6-(3-chloro-1-phenoxy)pyrimidine (1.7) in 80ml of acetonitrile and the mixture was stirred for 2 hours at 70° C.After the mixture had been cooled to 25° C., a precipitate was obtainedwhich was filtered off and washed. Recrystallization from ethyl acetategave 38% of theory of the title compound; m.p. 164°-165° C. (activeingredient example 1.006). The yield can be increased by furtherprocessing of the mother liquor and the wash phase.

3.31-Chloro-2-[[[4-chloro-6-(2,4-dichloro-1-phenoxy)pyrimidin-2-yl]aminocarbonyl]aminosulfonyl]benzene##STR23##

At 25° C., 4.9 g (23 mmol) of 1-chloro-2-isocyanatosulfonylbenzene wasadded to a suspension of 6.0 g (21 mmol) of2-amino-4-chloro-6-(2,4-dichloro-1-phenoxy)pyrimidine (1.44) in 70 ml of???. After refluxing for 5 hours and cooling to 25° C., the productprecipitated out. Washing and drying gave 70% of theory of the titlecompound; m.p. 222°-223° C. (active ingredient example 2.012).

3.41-Chloro-2-[[[4-[(3-methoxy)-1-phenoxy]-6-methylpyridin-2-yl]aminocarbonyl]aminosulfonyl]benzene##STR24##

At 50° C., 3.5 g (16.6 mmol) of o-chlorobenzenesulfonyl isocyanate wasadded to a suspension of 3.6 g (11.2 mmol) of1-amino-4-[(3-methoxy-1-phenoxy)]-6-methylpyrimidine (1.18) in 50 ml ofacetonitrile. After the homogenous solution had been evaporated down to5 ml, the product crystallized. Recrystallization with diethyl ethergave 4.8 g (95% of theory) of the title compound; m.p. 156°-158° C.(active ingredient example 4.001).

3.51-Chloro-2-[[[4-chloro-6-(4-chloro-1-phenoxy)-1,3,5-triazin-2-yl]aminocarbonyl]aminosulfonyl]-benzene##STR25##

A spatula tip of 1,4-diaza(2,2,2)bicyclooctane [DABCO] and 4.2 g (19.3mmol) of o-chlorobenzenesulfonyl isocyanate were added to a suspensionof 4.0 g (15.6 mmol) of2-amino-4-chloro-6-(4-chloro-1-phenoxy)-1,3,5-triazine (1.40) in 40 mlof acetonitrile, and the mixture was refluxed for 17 hours. After themixture had cooled it was filtered, and the product was washed with asmall amount of acetonitrile and dried. There was obtained 36% of theoryof the title compound; m.p. 187°-190° C. (active ingredient example9.006). The yield can be increased by further processing of the motherliquor and the wash phase.

The compounds given in Tables 1-12 were synthesized analogously to themanufacturing directions described above.

                  TABLE 1                                                         ______________________________________                                         ##STR26##                                                                    No.       (R.sup.3).sub.m                                                                            Melting point (°C.)                             ______________________________________                                        1.001     H            145-147                                                1.002     2-OCH.sub.3  179-181                                                1.003     3-OCH.sub.3  152-154                                                1.004     4-OCH.sub.3  170-175                                                1.005     2-Cl         175-177                                                1.006     3-Cl         164-165                                                1.007     4-Cl         175-180                                                1.008     2-NO.sub.2   142-148                                                1.009     3-NO.sub.2   200-205                                                1.010     4-NO.sub.2   213-215                                                1.011     2-CN         138-140                                                1.012     3-CN         157-165                                                1.013     4-CN         208-211                                                1.014     2-F          133-138                                                1.015     3-CF.sub.3   198-202                                                1.016     2-OCH.sub.3, 6-OCH.sub.3                                                                   120                                                    1.017     2-Cl, 4-Cl, 6-Cl                                                                           210-213                                                1.018     3-N(CH.sub.3).sub.2                                                                        165-170                                                1.019     2-Cl, 4-CF.sub.3                                                                           72-75                                                  1.020     2-CO.sub.2 CH.sub.3                                                                        167-170                                                ______________________________________                                    

                  TABLE 2                                                         ______________________________________                                         ##STR27##                                                                    No.       (R.sup.3).sub.m                                                                            Melting point (°C.)                             ______________________________________                                        2.001     2-Cl         183-185                                                2.002     3-Cl         180-185                                                2.003     4-Cl         211-216                                                2.004     2-NO.sub.2   207-211                                                2.005     3-NO.sub.2   183-188                                                2.006     4-NO.sub.2   210-215                                                2.007     2-CN         181-187                                                2.008     3-CN         172-176                                                2.009     4-CN         188-191                                                2.010     2-F          175-178                                                2.011     4-OCH.sub.3  159-163                                                2.012     2-Cl, 4-Cl   222-223                                                2.013     2-OCH.sub.3, 6-OCH.sub.3                                                                   98                                                     2.014     2-Cl, 4-Cl, 6-Cl                                                                           212-214                                                2.015     2-Cl, 4-CF.sub.3                                                                           213-215                                                2.016     3-N(CH.sub.3).sub.2                                                                        150-155                                                ______________________________________                                    

                  TABLE 3                                                         ______________________________________                                         ##STR28##                                                                    No.       (R.sup.3).sub.m                                                                            Melting point (°C.)                             ______________________________________                                        3.001     2-OCH.sub.3  158-162                                                3.002     3-OCH.sub.3  104-107                                                3.003     2-CN         157-159                                                3.004     3-CN         167-168                                                3.005     4-CN         193-195                                                3.006     2-OCH.sub.3, 6-OCH.sub.3                                                                   195-197                                                3.007     2-NO.sub.2   179-180                                                3.008     3-NO.sub.2   184-185                                                3.009     4-NO.sub.2   193-196                                                3.010     3-CF.sub.3   153-156                                                3.011     3-Cl         150-151                                                3.012     4-Cl         193-194                                                3.013     2-F          152-154                                                3.014     3-N(CH.sub.3).sub.2                                                                        177-180                                                3.015     2-Cl         148-150                                                ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                         ##STR29##                                                                    No.       (R.sup.3).sub.m                                                                            Melting point (°C.)                             ______________________________________                                        4.001     3-OCH.sub.3  156-158                                                4.002     2-OCH.sub.3, 6-OCH.sub.3                                                                   199-203                                                4.003     2-F          171-173                                                4.004     2-CN         190-195                                                4.005     3-CN         206-208                                                4.006     4-CN         200-202                                                4.007     2-Cl         188-190                                                4.008     3-Cl         172-173                                                4.009     4-Cl         192-193                                                4.010     2-NO.sub.2   204-205                                                4.011     3-NO.sub.2   196-198                                                4.012     3-CF.sub.3   167-168                                                4.013     3-N(CH.sub.3).sub.2                                                                        85-90                                                  ______________________________________                                    

                  TABLE 5                                                         ______________________________________                                         ##STR30##                                                                    No.    (R.sup.3).sub.m    Melting point (°C.)                          ______________________________________                                        5.001  4-OCH.sub.3        146-148                                             5.002  2-Cl               145-150                                             5.003  3-Cl               146-150                                             5.004  4-Cl               156-160                                             5.005  2-OCH.sub.3        104-108                                             5.006  3-OCH.sub.3        148-152                                             5.007  2-OCH.sub.2 CH.sub.3                                                                             177-180                                             5.008  4-OCH.sub.2 CH.sub.3                                                                             152                                                 5.009  2-OCH.sub.3, 4-CH.sub.3                                                                          167                                                 5.010  3,4-(OCH.sub.3).sub.2                                                                            154-155                                             5.011  2-OCH.sub.3, 4-(E)CHCHCH.sub.3                                                                   173-175                                             5.012  2,3-(OCH.sub.3).sub.2                                                                            155                                                 5.013  3,4,5-(OCH.sub.3).sub.3                                                                          183-184                                             5.014  3,5-(OCH.sub.3).sub.2                                                                            177-178                                             5.015  3,4-(OCH.sub.2 O)  180-183                                             5.016  2-t.-C.sub.4 H.sub.9, 4-OCH.sub.3                                                                179-182                                             5.017  4-OCH.sub.2 C.sub.6 H.sub.5                                                                      145-146                                             5.018  2-OCH.sub.2 C.sub.6 H.sub. 5                                                                      95-100                                             5.019                                                                                 ##STR31##         163-164                                             5.020                                                                                 ##STR32##         196-202                                             5.021  3-CH.sub.3, 4-CH.sub.3                                                                           176-178                                             5.022  4-SCH.sub.3        116-120                                             5.023  2-CH.sub.3, 4-SCH.sub.3                                                                          177-179                                             5.024  2-Cl, 4-OCH.sub.3  180                                                 5.025  2-OCH.sub.3, 4-C(O)CH.sub.3                                                                      114-116                                             5.026  2-OC.sub.2 H.sub.5, 4-Cl                                                                         154-158                                             ______________________________________                                    

                  TABLE 6                                                         ______________________________________                                         ##STR33##                                                                    No.      (R.sup.3).sub.m                                                                             Melting point (°C.)                             ______________________________________                                        6.001    2-Cl          164-170                                                6.002    3-Cl          123-125                                                6.003    2-OCH.sub.3    95-100                                                6.004    3-OCH.sub.3   75-80                                                  6.005    4-Cl          177-182                                                6.006    3,4-(OCH.sub.2 O)                                                                           124-134                                                6.007    2-t.-C.sub.4 H.sub.9, 4-OCH.sub.3                                                           183-187                                                6.008    4-OCH.sub.2 C.sub.6 H.sub.5                                                                 145-146                                                6.009    2-OCH.sub.2 C.sub.6 H.sub.5                                                                 162                                                    6.010                                                                                   ##STR34##    173-177                                                6.011    3-CH.sub.3, 4-SCH.sub.3                                                                     163-165                                                6.012    2-Cl, 4-OCH.sub.3                                                                           188                                                    6.013    4-SCH.sub.3   145-146                                                6.014    2-CH.sub.3, 4-SCH.sub.3                                                                     179-184                                                6.015    2-OCH.sub.2 CH.sub.3, 4-Cl                                                                  161-162                                                ______________________________________                                    

                  TABLE 7                                                         ______________________________________                                         ##STR35##                                                                    No.    R.sup.1  R.sup.2  (R.sup.3).sub.m                                                                      Melting point (°C.)                    ______________________________________                                        7.001  CO.sub.2 CH.sub.3                                                                      Cl       2-OCH.sub.3                                                                          146-150                                       7.002  CO.sub.2 CH.sub.3                                                                      Cl       2-Cl   185-188                                       7.003  CO.sub.2 CH.sub.3                                                                      CH.sub.3 4-OCH.sub.3                                                                          193                                           7.004  Cl       Cl       2-Cl   200-204                                       7.005  Cl       Cl       2-OCH.sub.3                                                                          123-127                                       7.006  Cl       CH.sub.3 4-OCH.sub.3                                                                          207-208                                       ______________________________________                                    

                  TABLE 8                                                         ______________________________________                                         ##STR36##                                                                    No.        (R.sup.3).sub.m                                                                         Melting point (°C.)                               ______________________________________                                        8.001      2-OCH.sub.3                                                                             184-187                                                  8.002      3-OCH.sub.3                                                                             162-165                                                  8.003      4-OCH.sub.3                                                                             210-212                                                  8.004      2-Cl      152-156                                                  8.005      3-Cl      176-179                                                  8.006      4-Cl      165-170                                                  8.007      4-CN      168-170                                                  8.008      2-Cl, 4-Cl                                                                              173-175                                                  ______________________________________                                    

                  TABLE 9                                                         ______________________________________                                         ##STR37##                                                                    No.         (R.sup.3).sub.m                                                                        Melting point (°C.)                               ______________________________________                                        9.001       2-OCH.sub.3                                                                            173-178                                                  9.002       3-OCH.sub.3                                                                            159-162                                                  9.003       4-OCH.sub.3                                                                            162-167                                                  9.004       2-Cl     189-193                                                  9.005       3-Cl     165-169                                                  9.006       4-Cl     187-190                                                  9.007       2-CN     174-176                                                  9.008       3-CN     186-188                                                  ______________________________________                                    

                  TABLE 10                                                        ______________________________________                                         ##STR38##                                                                    No.     R.sup.2 X       (R.sup.3).sub.m                                                                      Melting point (°C.)                     ______________________________________                                        10.001  Cl      S       2-OCH.sub.3                                                                          209-211                                        10.002  Cl      O       4-Cl   >230                                           10.003  Cl      O       3-Cl   215-225                                        10.004  Cl      O       2-Cl   195-198                                        10.005  Cl      O       4-OCH.sub.3                                                                          210-215                                        10.006  Cl      O       3-OCH.sub.3                                                                          182-188                                        10.007  Cl      O       2-OCH.sub.3                                                                          155-160                                        10.008  OCH.sub.3                                                                             O       4-OCH.sub.3                                                                          155-158                                        ______________________________________                                    

                  TABLE 11                                                        ______________________________________                                         ##STR39##                                                                                                        Melting point                             No.    R.sup.1     (R.sup.5).sub.n                                                                       (R.sup.3).sub.m                                                                        (°C.)                              ______________________________________                                        11.001 CO.sub.2 (i-C.sub.3 H.sub.7)                                                              H       3-OCH.sub.3                                                                            130-133                                   11.002 CO.sub.2 CH.sub.3                                                                         5-F     3-OCH.sub.3                                                                            156-158                                   11.003 CO.sub.2 CH.sub.3                                                                         5-F     2-OCH.sub.3                                                                            125-127                                   11.004 CO.sub.2 CH.sub.3                                                                         3-Cl    3-OCH.sub.3                                                                            132                                       11.005 CO.sub.2 CH.sub.3                                                                         3-Cl    4-OCH.sub.3                                                                            192-194                                   11.006 CO.sub.2 CH.sub.3                                                                         5-F     4-OCH.sub.3                                                                            178-179                                   11.007 CO.sub.2 (CH.sub.2).sub.2 Cl                                                              H       3-OCH.sub.3                                                                            148                                       11.008 CO.sub.2 (CH.sub.2).sub.2 Cl                                                              H       2-OCH.sub.3                                                                            166-167                                   11.009 CO.sub.2 (CH.sub.2).sub.2 Cl                                                              H       4-OCH.sub.3                                                                            172-173                                   11.010 CO.sub.2 (i-C.sub.3 H.sub. 7)                                                             H       2-OCH.sub.3                                                                            143-145                                   11.011 CO.sub.2 CH.sub.3                                                                         3-Cl    2-OCH.sub.3                                                                            168-170                                   11.012 CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                        H       2,6-(OCH.sub.3).sub.2                                                                  70-80                                     ______________________________________                                    

                  TABLE 12                                                        ______________________________________                                         ##STR40##                                                                    No.   R.sup.2   X       (R.sup.3).sub.m                                                                       Melting point (°C.)                    ______________________________________                                        12.001                                                                              CO.sub.2 CH.sub.3                                                                       F       2-OCH.sub.3                                                                           161                                           12.002                                                                              CO.sub.2 CH.sub.3                                                                       F       3-OCH.sub.3                                                                           143                                           12.003                                                                              CO.sub.2 CH.sub.3                                                                       F       4-OCH.sub.3                                                                           167-170                                       12.004                                                                              CO.sub.2 CH.sub.3                                                                       CF.sub.3                                                                              2-OCH.sub.3                                                                           115                                           12.005                                                                              CO.sub.2 CH.sub.3                                                                       CF.sub.3                                                                              3-OCH.sub.3                                                                           177-178                                       12.006                                                                              CO.sub.2 CH.sub.3                                                                       CF.sub.3                                                                              4-OCH.sub.3                                                                           188                                           12.007                                                                              CO.sub.2 CH.sub.3                                                                       CF.sub.3                                                                              3-N(CH.sub.3).sub.2                                                                   176-177                                       12.008                                                                              CO.sub.2 CH.sub.3                                                                       OC.sub.2 H.sub.5                                                                      2-OCH.sub.3                                                                           109                                           12.009                                                                              CO.sub.2 CH.sub.3                                                                       OC.sub.2 H.sub.5                                                                      3-OCH.sub.3                                                                           71-75                                         12.010                                                                              CO.sub.2 CH.sub.3                                                                       OC.sub.2 H.sub.5                                                                      4-OCH.sub.3                                                                           128-131                                       12.011                                                                              CO.sub.2 CH.sub.3                                                                       OC.sub.2 H.sub.5                                                                      3-N(CH.sub. 3).sub.2                                                                  142                                           ______________________________________                                    

USE EXAMPLES

The action of the sulfonylureas of the formula I on the growth of plantsis demonstrated by the following greenhouse experiments.

The vessels employed were plastic flowerpots having a volume of 300 cm³and filled with a sandy loam containing about 3.0% humus. The seeds ofthe test plants were sown separately, according to species.

The plants were kept in the greenhouse in accordance with their specificrequirements (10°-25° C., and 20°-35° C.). The experiments were run forfrom 2 to 4 weeks. During this period the plants were tended and theirreactions to the various treatments assessed.

For the postemergence treatment, plants were selected which had beensown in the vessels and grown there, or they were grown separately asseedlings and transplanted to the vessels a few days before treatment.

The plants were grown, depending on growth form, to a height of 3 to 15cm before being treated with the compounds suspended or emulsified inwater, and sprayed through finely distributing nozzles. The applicationrates for postemergence treatment were 0.5, 0.25 and 0.125 kg/ha.

For the preemergence treatment, the formulated active ingredients wereapplied to the surface of the soil immediately after the seeds had beensown. The compounds were emulsified or suspended in water as vehicle,and sprayed through finely distributing nozzles. After the agents hadbeen applied, the vessels were lightly sprinkler-irrigated to inducegermination and growth. Transparent plastic covers were then placed onthe vessels until the plants had taken root. The cover ensured uniformgermination of the plants, insofar as this was not impaired by theactive ingredients. The application rate in this treatment method was0.125 kg/ha.

The assessment scale was 0 to 100, 100 denoting nonemergence or completedestruction of at least the visible plant parts, and 0 denoting nodamage or normal growth.

The plants employed for the experiments were Amaranthus retroflexus,Chrysanthemum corinarium, Cyperus iria, Galium aparine, Helianthusannuus, Sesbania exaltata, Stellaria media and Triticum aestivum.

Compounds 1.002, 1.003 and 1.006, applied postemergence at rates of 0.5and 0.25 kg/ha, combat unwanted plants very well.

Compounds 5.005 and 6.003, applied pre- and postemergence at a rate of0.125 kg/ha, provide excellent control of unwanted broadleaved plantswithout causing any appreciable damage to the crop plant wheat.

We claim:
 1. A substituted sulfonylurea of the formula I ##STR41## wherethe substituents and indices have the following meaning: X is oxygen orsulfur;Z is nitrogen R¹ is halogen, C₁ -C₄ -alkoxycarbonyl which maycarry from one to three of the following radicals: halogen, C₁ -C₄-alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio and/or C₁ -C₄-haloalkylthio; C₁ -C₃ -alkoxy which may carry from one to three of thefollowing radicals: halogen, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄-alkylthio, and/or C₁ -C₄ -haloalkylthio; or a radical --CONR⁶ R⁷, whereR⁶ is hydrogen, C₁ -C₈ -alkyl or C₁ -C₆ -alkoxy and R⁷ is hydrogen or C₁-C₈ -alkyl; R² is halogen; C₁ -C₄ -alkoxy or C₁ -C₄ -alkyl which mayeach carry from one to three of the following radicals: halogen, C₁ -C₄-alkoxy and/or C₁ -C₄ -alkylthio; R³ is C₁ -C₄ -alkyl. C₁ -C₄ -alkoxy,C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, C₁ -C₄-haloalkylthio, halogen, cyano, nitro, amino, mono-C₁ -C₄ -alkylamino,di-C₁ -C₄ -alkylamino, C₂ -C₆ -alkenyl, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄-alkanoyl or benzyl; a member of the group consisting of pyrrolidinyl,piperidinyl, morpholinyl and thiomorpholinyl which is attached by itsnitrogen atom or, bonded to adjacent ring positions, --OCRR'O--, where Rand R' are each hydrogen or C₁ -C₄ -alkyl; R⁴ is hydrogen or C₁ -C₄-alkyl; R⁵ is halogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkyl, C₁-C₄ -alkylthio or C₁ -C₄ -haloalkyl; m is from 0 to 3 or, when R³ ishalogen, from 0 to 5, differences among the R³ radicals being possiblewhen m is 2 or 3; and n is from 0 to 2, a difference between the R⁵radicals being possible when n is 2;and environmentally acceptable saltsthereof.
 2. A herbicidal composition containing a herbicidally effectiveamount of a substituted sulfonylurea as set forth in claim 1, or a saltthereof, and conventional formulation auxiliaries.
 3. A process forcombating the growth of unwanted plants, wherein a herbicidallyeffective amount of a substituted sulfonylurea as set forth in claim 1,or a salt thereof is applied to the plants and/or their habitat.
 4. Acomposition for influencing the growth of plants, containing agrowth-regulating effective amount of a substituted sulfonylurea as setforth in claim 1, or a salt thereof, and conventional formulationauxiliaries therefor.
 5. A process for influencing the growth of plants,wherein a growth-regulating amount of a substituted sulfonylurea as setforth in claim 1, or a salt thereof, is applied to the plants and/ortheir habitat.